First Night With Miss Melissa

Author's note

I finally meet Miss Melissa for real and practice being a queer and homoflexible submissive male. And house boy.

We're a go

I'm meeting Miss Melissa in person. It's really happening. I think she was more excited than me because she kept texting the days left from ten days out. I was still into my routine and regimen. I was jerking twice a day most times, and a lot more of it was gay porn. Most of it was gay porn. I was finishing to gay porn. I was really into muscle bottoms, and they were strongly resonating with me. I like the aggressiveness of the fucking while still bottoming. They were submissive, but manly and masculine, and I really liked that. Female focused gay encouragement captions were the overwhelming majority of that type of content out there but wasn't really working for me anymore. Other than Miss Melissa, I just didn't feel any attraction to cis girls anymore. I was still interested in sex with and dating tgirls, but there just weren't any in my area. Miss Melissa checked in with me one last time while I was packing. She actually called on the phone.

MM - You packed?

boi - Just about! Watching porn and packing.

MM - I'm very intrigued by these muscle bottoms that you've been showing me. Do you think you fit in with them?

boi - I don't think I'm that jacked up, but I like how they're not all sissy about getting fucked. It's active bottoming that I like.

MM - You're fit though. I could see you in that role with a dominant male. boi - I'd try it. I'd be open to being bound too.

MM - Maybe that's something we'll have to try here then. We won't do everything all at once so don't worry.

boi - Sure, there's plenty of time.

MM - Ah, so soon! Tomorrow! Don't text me unless there's any delays. I want to be thinking about you alllllll day!

I know there was only so much we could do, but I was hoping I would be able to cross a line for real by visiting her. It was highly unusual for me to actually check a bag, but there's no way my enema kit, plug, ring, and huge dildo were going to make it through with a carry on. I actually thought about just wearing the cock ring because it's leather, but it's got metal snaps. Also, the airport is a small one, and I just really couldn't be seen being patted down for a cock ring. I got 2, free checked bags anyway. No big deal. All packed, and I went to bed early for a big travel day.

Finally

Traveling takes all day no matter what. I didn't get up at the crack of dawn. I'm too old for that. Departure was mid morning. Shockingly, there were minimal delays, and I arrived mid evening. I texted Miss Melissa to just let her know I landed and received a flood of emojis.

She greeted me when I got out of the gate area with a huge grin on her face. She wrapped me up and planted a big kiss on my cheek. 'YAY!'

That's all she could get out. I laughed. 'Good to be here finally.'

'Let's get your bag.'

We of course had to wait a few minutes for the carousel to kick into gear. She put her arm around me. She's actually taller than me by about two inches or so. 'How was the flight?' She asked.

I shrugged my shoulders. 'Routine for a change. Just a few minutes delay. The layover was long, but I just went to the lounge.'

'How did you get into the lounge?'

'You have to have the right credit card, but you still have to pay. For close to three hour layover though, it's worth it.'

Did you have any drinks?'

'Several.'

The bell rang, and the bags spilled out. I retrieved mine soon enough. 'That's it? Small bag. You could almost fit everything in your carry on.'

'I don't think I would want anyone seeing all this going through the xrays in case they wanted to open it up.'

'They'd all know you're a kinky queer.'

She didn't say it loud, just normal speaking voice, but it is a crowded area. I reddened in humiliation, and she knew it.

She pulled me in for another hug and whispered in my ear. 'Hey. That other guy is gone now. You are smoothboi now. This is why you're here.'

I just nodded because my throat was a little dry. I took a deep breath.

She grinned again. 'Let's get the hell out of here, so I'm not charged another hour in the lot.'

We had a little over an hour ride, but not much traffic. 'Are you tired?' She asked.

'Worn out more than tired. A little cramped.'

'Ok, I didn't have anything planned tonight anyway. Let's just relax. I don't think I want to give you any weed if you've been drinking.'

'No, I figured,' I replied, 'what is the plan for tomorrow?'

'You're going to do housework. And vacuum. I'm going to lounge around and fully enjoy having a nude houseboi at my disposal.'

'Works for me.'

'I'd like you to douche out in the morning. I know you're going to do a spectacular job, but I'm dying to peg the lights out of you.'

'You won't be disappointed. I promise.'

'This is a dumb question, but you know how to cook on a grill? Not just char the shit out of everything. Actually cook.'

'Yes, I know what you mean. I've got a list of recipes with proper temperatures and times.'

'Excellent. I thought maybe we'd keep it low key. I figured you're going to be a little tired from housework, but maybe tomorrow night, weed?'

'Let's see how I feel. I want to, but I feel like I have to be ready.'

'No problem. And only just a little. I want us to go to the nude beach the next day and get you in a more confident homoflexible space. How you felt at Dore but more intense.'

'I'm with that. I've been reading up on cruising and where to suck cock at the beach.'

'ooooh. Have you now? Maybe I'll do that while you clean the house tomorrow. But don't set yourself up. Let's just let it happen. I want you to suck all the cocks, but just going there and showing yourself as a gay male is an accomplishment too.'

'No, I know, but I want to take somewhat of an active role.'

'Good boi. You wanna take your clothes off?'

'In the car?'

'Yes, in the car. It's nighttime, and we're driving right home into the garage. If we get into the neighborhood, you can always slip them back on if there's anyone out.'

I shrugged again. 'All right.' I actually didn't have to untie my shoes because I was wearing shorts that were wide enough in the leg. I slipped off my shorts and my shirt and just put them on the mat near the door. I could always get the shirt on fast if I had to.

'Mmmmm.' She rubbed up and down my thigh. I'm completely shaved smooth. She stretched her hand out and cupped my balls.

'So smooth. There's a full load in there.'

'I jerked before I left, and I'm kind of worn out like I said.'

'Let's get home and see how you feel. You might not be able to get it up in front of a woman anymore! Hee.'

'Probably not, but you're not just any woman.'

'No, I'm your Mistress now. I know you'll get it up.' She kept her hand on my thigh as she drove.

'Do you think you would have worn the cock ring if it was a bigger airport like San Francisco?'

'I think I would have probably put it in the carry on and then put it on after security. It doesn't look like any weapons, but they might have wanted to open the bag to see.

'What would you say if they caught you?'

'Probably I lost a bet or you dared me to wear it. In San Francisco I doubt they'd really make a big deal out of it.'

'No. I don't even think they'd care if you wore it through security'.

I just nodded. 'Where I'm living though isn't great for that.'

'No. It's too bad. If you stayed in San Francisco it would have been way more open.'

'I'd probably be way more active than just going to munches.'

'Oh, sure, and you'd eventually get to the gay nude beach. And of course all the fairs.'

We arrived home shortly after. No one was outside in the fading light, and I didn't have to bother putting clothes on as we parked in the garage.

Wrapping up the day

Miss Melissa had a ranch house. Not too big, several bedrooms, living/dining room, and two bathrooms. One was in the bedroom part of the house and then off the living room near the kitchen. The front door opened from the kitchen and dining area and then another back door in the living room to a small patio and outside. The garage was on the living room side of the house, on the left, if facing the house. The yard had a closed in fence on one side of the house from the back exit.

'Follow me.' She took me to the guest room. It was small, but fine. Closet, bed, nightstand and a small table. I put the bags in the closet.

'Wait. Show me your stuff.'

I took out the bag with everything in it. I handed her the plug. It's an njoy XL. It's about a pound and a quarter.

'Ooof. It's heavy! I can't believe you put this in every day!'

'It took a while to work up to it, but your body gets used to the penetration.'

'I so want to see you put it in, but it's too late for today.'

'Once I put it in, I would rather be able to keep it in for a while than have to take it out sooner. I plan on wearing it all day tomorrow.'

'You can go that long? All day?'

'Once I empty out.'

'Oooh, show me the enema kit.'

It was just a bulb and a removable plastic stalk. I got it a while ago because it was cheap. I haven't actually needed to use it much. I hadn't been fucked a lot.

'I'd like to do this to you,' She said firmly. 'I think it would be very humiliating for you.'

'If you want to go that far.'

'I think stripping away your limits will help you submit to your own homosexuality...ooooh, what's this?' She held up the riding crop.

'I didn't know if you had one, and I've gotten comfortable with it now.'

'I do not. Let me take a just few swats. I won't go hard. Get on the bed and bend over.'

I complied and bent over for her on the bed. 'Mmmm. Look at that smooth asshole.' She ran a finger lightly over my hole making me shiver and tingle.

'Or is it a cunt? Because that's how you fuck now.'

'They call it muscle cunt.' I replied.

'oooh I like. We're going to be using that from now on. You'll ingrain that on yourself now. I want you immersed. Reflexively, you'll identify as a muscle cunt.'

'I want to. I feel like it's happening so fast even though I've taken so long.'

'We've moved kind of quick though since we decided you were coming out here. It's obvious you needed this. Just a little bit of discipline is revealing who I think you really are. But that's why you have a Mistress now. To guide you where you need to go. So fun!'

She gently glided the crop down my crack over my asshole; my cunt. My balls tightened and my cock swelled a little.

She did the same around my ass and then just a mild smack-smack. I gasped, but it was a pleasurable gasp.

'Was that all right? Too hard?'

'No, totally fine.'

She did it a few more times, each as pleasurable as the last. I had a good semi now.

'I see you getting hard. Pain slut. I love it. Reach back and spread. One more pass.'

I reached back and spread my ass wide.

'Arch your back more; expose yourself to me.'

I got more up on my knees and turned my ass up as much as I could. I reached back so I could spread. She slid the crop down again over my cunt and then lightly swatted my hole sending a jolt right to my cock. I grunted slightly.

'Yeah you like.' You don't have to hold back with me. Let your body respond. You don't have to think.' She swatted my cunt a few more times. I moaned and arched my back with each stroke.

'That's it. I bet this would be even better if you were plugged.'

'Yeah, I did it with Jane, and I was leaking a little.'

'Oh? We'll try that tomorrow. You want to take a shower? I'd like to watch you. We could have a drink after for a bit.'

'Sure. That will help me sleep too.'

She followed me into the bathroom and sat on the toilet as a chair to watch me. I turned the water on and waited a minute or so for the water to warm up. The shower had glass doors so Miss Melissa could watch.

As I stepped in she asked, 'Have you thought anymore about being homoflexible?'

'I actually like it. I changed my fetlife to queer and homoflexible.'

'Oh really? It turns me on so much when you get active. But I don't think you're really getting me. I think you *are* homoflexible. You always were.'

'I never had gay urges before.'

'Until you did. Then you only had gay sex. You have feelings for me, but I'm the only woman in your life in this way. I've been the only woman in your life for the last ten years.'

'I always thought of it as me growing into homoflexible.' I shut the water off, and

Miss Melissa took a towel off the hook. She slid open the door and handed it to me. 'This one is clean. Just use it for yourself.'

'You going to want me to do laundry at some point.'

'Probably after the beach. Would you like a drink still?' I dried off and hung the towel up.

'Sure.'

We went to the kitchen, where she opened up a lower draw with some booze bottles and pulled out Jack Daniels. She put it on the kitchen and reached up to open a cupboard with several glasses.

'This is where you're taking over as the houseboi. Get to work.'

I took the glasses out and poured some of the Jack in each.

'I guess it should be house boy now, shouldn't it?' I could tell by the inflection what she meant.

'I'd like that better. Ice?'

'Yes.'

I plunked a cube in each, and she led me to the living room. She sat on a chair, like an accent chair, in the corner and indicated for me to sit next to her on the floor.

'Can you kneel? Or just sit normal next to me,' she said as I winced when I got down to kneel. She draped her left hand over my shoulder.

'And it should be smooth boy now,' she added.

'Yes. I've been changing my name across platforms already.'

'We're going to be only calling you smooth boy this week. That's what I meant. You may have grown into smooth boy, but part of him was there waiting to emerge.'

'I think we're coming to the same realization about me from different sides because this is really who I am right now.'

'It's so hot that you're so smart. Let's just be in that moment, that feeling for you, right now. And lots of gay men come out when they get older. Even after marrying women and having kids. Something just flipped a switch or a trigger or something. I mean, I'm kind of bi now myself, but I never thought about it before. And poly.'

'Dore Alley had to be my trigger. I was moving more homo with learning about bdsm but there was something about really being there.'

'Oh, for sure, and that was the first time we talked on the phone! My point was that had you gone in 2007 or 2010 or whenever, you would have still become aware of your own homosexuality.'

'Maybe. It was the going on my own and getting out there that was really refreshing.'

'Refreshing is an interesting choice.'

'Well, it really was. Although, I disagree a little. I think it could have only happened then.'

'Why?'

'I needed the time to fuck all those girls to realize being hetero wasn't working for me. I got frustrated and bored.'

'Because you were always homoflexible but didn't have a way of expressing it. You body was responding. Look.'

She pointed at my swelling cock.

'Your body is still responding. I want you to submit fully to those urges this week.'

I just nodded as I sipped my drink.

'You know you can't jerk without my permission.' She wasn't asking. 'I know.'

'Your obedience will bring you release and pleasure.'

'I think that's the best part'.

'What's that?'

'Obedience and discipline. Really submitting to you. Finally.'

'It's just as exciting for me too. This isn't like with my sissy at all. Completely different dynamic. Refreshing!'

She took another sip on her drink. 'Actually, I want to see you jerk now.'

'Do you want me to do the plug and all that then?'

'Is it tough to only keep it in a short time?'

'Yeah because I need to refract before I can take it out.'

She looked thoughtful as she drank some more. 'Let's put on the ring and the chain. You don't have to wear the plug. I'm going to finger your cunt.'

Now I got excited. 'All right.' I swigged down the booze and got up to go get my stuff. I stopped in the kitchen to rinse it out and went to put on the ring and chain.

I returned shortly and presented myself. 'Hah? How do I look?'

Her eyebrows shot up and a wave of lust washed over her face. 'Wow. You look gay as fuck and hot as fuck. You got to wear that to the beach. We're going to get a lot of attention!'

'For sure.' I replied. Not to brag, but I have a flat stomach and some tone to me. The chain accentuates my features.

'So how do we do this?' She asked. 'What do you normally do? Wait. Come here and stand in front of me.'

I did as instructed. She reached out to feel the cock ring and slide her finger around it. She cupped my balls. 'Does it hurt that tight? Your balls feel so full.'

'No, I like the feeling. I can feel it but it's not distracting.'

'I still say this chain is a trend for queers.'

'I've worn it out for errands a few times. With the ring.'

Her eyes widened. 'You've definitely earned some release just from being so proactive. Anyone see?'

'No, I'm too skittish for around there. If I was somewhere else, I might have been more showy.'

'So what do you usually do?'

'I sit at the desk or on the couch and look at porn on the tablet to get hard, and then when I'm closer I lie on the couch and let it rip. I have the plug in, so I can still look on the tablet with one hand.'

She got up. 'Sit down over here in front of the chair.' I did and spread my legs wide and sort of crossed them at my feet.

She sat down next to me. 'Go ahead. Oh. Let me switch.'

I was slowly stroking with my right hand, and she was on the same side, so she moved and sat down on my left. I resumed stroking.

'Could I touch you?' She smirked. 'Or will a woman turn you off? Hee.'

'Sure. Do you want me to take my time or just go?'

'Go at your own pace. I'm really just enjoying your body.' She was lightly stroking my chest then over my nipples. 'Are they always this hard? Can I pinch them?'

'Yes please. They are all the time.' She gave a light pinch and a tug.

'Good?'

'Yes. Great.' She kept circling around my chest and down to my stomach, pinching and pulling as I slowly got more erect.

She was practically purring. 'Is this too much? Am I distracting you?'

I had closed my eyes and was breathing deeper. 'No, this is great. I don't want to cross any boundaries with your sissy here though.'

'So thoughtful. You're going to make me swoon. No, he's fine. You might see him this week. We had a longer conversation about our relationships; you and me and him and me. I assured him you wouldn't be fucking me or eating me out, and I can't eat your cunt. Sadly. He doesn't like being pegged, and he knows I really am into it. I also promised I wouldn't touch your cock either. And you couldn't fuck a woman anyway anymore. You're too immersed in your own homosexuality now.'

She looked down and grinned wildly as I stroked to full hardness and my chest reddened. I quickened up the pace on my cock. 'You like that. So deeply humiliating for you.'

I exhaled deeply and just nodded as I squeezed my cock and a little precum emerged.

She giggled. 'You ever think about piercing your nipples? Your chest is so toned and nice.'

'They show through my clothes so much though as it is. I'd be worried about work. I like wearing tighter clothes to show off my body.'

'Hmm. I wonder if there's fakes like clip on earrings? Something small.' She was pinching and tugging both. It was an incredible sensation that was shooting down to my balls. 'That would be a very gay look and very hot. Look into that.'

'Not as fun if you can't really show them off though.'

'You could wear them on your getaways. We want you to get just a little more open and out about being homoflexible. The more accepting you are the more attractive you've been getting. And I know you feel way more sexy as you're accepting yourself. Maybe you'd get some man attention. Jerking together back in your hotel room.'