I’m sitting on my sofa; the TV has the news on, but I’m not really paying attention. I’m waiting for my phone to buzz and play the message tone. My phone does buzz, but it’s not the message tone; it’s another alert for some sort of app.
My excitement grows, then I hear the message tone. I grab my phone and look at the message. It’s from her.
Mistress
Hi.
How are you?
Me
Hi, I’m good, thank you.
Mistress
So you want to experience an evening with a mistress? Are you ready to be my slave and give me utter control over you?
Me
Yes. I’ve never experienced anything like this before, so I’m not sure what happens.
Mistress
Well, you’ve taken the first step, talking to me. Are you ready for your first task?
Me
Yes, I’m ready, I think.
Mistress
Well, you are either ready or you aren’t. So which is it?
Me
I’m ready.
Mistress
The first task is simple; I want you to take a picture of yourself in the mirror, fully naked.
Me
Fully naked?
Mistress
Yes, fucking naked. But your face must also be in the picture.
Me
Okay.
I walk to my bedroom, which has a full-length mirror. I take my clothes off; my cock is hard. I take a picture and look at it; not too bad.
I put my clothes back on and send her the picture.
Mistress
You’re very cute. Well done. I’d love to put that cock in a chastity cage.
‘Cute’ wasn’t exactly the word I was looking for, but the praise did make me feel good. My cock wasn’t huge; it was above average and has a good girth to it, or so I’d been told.
Mistress
So you need to get your SRN.
Me
I’m sorry, what’s that?
Mistress
Slave Registration Number. It’s a unique number assigned to you. Think of it like a dog register; if you give someone the number, they can find out who owns you, per se.
Me
Okay, I’ll do it now.
Mistress
I’ll be waiting.
I open my laptop and go onto the link the mistress sent me. I fill in all the information that’s needed and pay the signing-up fee. Once I have my number, I text the mistress back.
Me
Here is my SRN.
Mistress
Good boy. Now you can have access to my dungeon.
My cock twitches at the praise and the mention of a dungeon.
Me
You have a dungeon!?
Mistress
Of course I do, cutie. How else do you think I play with my slaves? Here is what it looks like.
She sends me pictures of her dungeon. I’m not sure what I was expecting, but it wasn’t what I saw. It was a brightly lit room with stone walls and wooden floors. There was a cabinet with an assortment of dildos and toys; I feel my cock grow harder. There is a black four-poster bed with red bedding. There are tables and chairs, not the kind you’d sit down and eat at, more the kind you are strapped to. There was a hanging harness, there was a wooden X attached to the wall, and there were four cuffs on each of the ends.
Me
That’s your dungeon?
Mistress
Yes. Do you like it?
Me
What’s not to like? It looks like a lot of fun could be had.
Mistress
Only good boys get to have fun.
Me
And what happens to boys who aren’t good?
Mistress
They get punished until they are good boys.
So do you want to book a session?
Me
How much is it, and how long is it for?
Mistress
It’s $300 for a session, and the session lasts for as long as you take it or until you say a safe word.
Me
I’d like to book a session, please.
Mistress
I will need payment up front in case you decide you want to cancel; I’m sure you understand.
Me
Yes, that’s fine.
I send her the money, and we make an appointment for the following Saturday.
We plan to meet on Wednesday for a coffee; this is to make sure I am who I say I am and that she is comfortable with going ahead with the session.
I’m sitting at the table with a caramel latte. I’m wearing a black T-shirt and black snapback. I sent her a picture before I left the house so she would be able to recognise me. The two full tattoo sleeves and my fully tattooed neck were also a giveaway.
I look at every woman that comes into the shop; I’m sitting at a table that’s facing the door so as not to look like a total creep. I’ve seen a vague picture of the mistress, but it wasn’t very clear.
I don’t know why, but the thought just dawned on me. This could be a total setup, and I’ve just lost $300, or it could be a complete catfish moment. I fidget, trying to push those thoughts from my head.
I see a very attractive brunette woman walk towards me. Her piercing blue eyes don’t leave mine; it’s her. She is wearing gym leggings and trainers with a loose jumper. I don’t know what I expected, maybe full latex. But that’s the mistress. I stand up and pull her chair out.
“Thank you very much. Very nice to meet you, Matt. You are very cute.”
My palms are sweaty. “Thanks. Nice to meet you too…” I don’t actually know what to call her.
“Mistress Natalie. Out in public, you can just call me Natalie.”
“Well, it’s nice to meet you as well, Natalie.”
She takes a sip of her coffee, studying me over the rim of her cup. “So Matt. Why do you want to experience a mistress?”
“I was looking through some porn the other week, and I watched a mistress video; it turned me on a lot. So I watched some more and then decided that I wanted to experience it."
“So do you enjoy trying new things?” she asks me, her blue eyes never leaving mine.
“I’ll try anything once; otherwise, how will you know if you like it, right?” I take a sip of my latte.
“So you’d say you are open-minded?” she asks after taking a sip of her coffee.
“Well, yeah, I guess so. I’m sorry I have to say this, but you are extremely beautiful.” She is mesmerising to look at. I would tell her this, but I’d happily pay double what I’ve paid.
“Thank you, that’s very sweet. Did you do the tasks I assigned you?”
“I did.” I noticed her look at my hands on the table. I was told I have to cut my fingernails and toenails; I also had to trim my pubic hair. I always kept it maintained anyway, so that wasn’t an issue. “I took pictures of my toe and pubic hair.”
“Show me.” She commands. I take my phone out and open up the camera roll and hand her the phone. “Well done, that is a lovely cock.” As if on cue, I feel my cock twitch and stiffen a little.
“I can’t wait to put that in a cage. Do you live close to here?” The question takes me by surprise.
“Yes, a five-minute walk.” She stands up.
“Let’s go back to your house.” It isn’t a question; she is telling me we are going to my house. Me and my growing cock are more than happy to take her.
I open the door and indicate for her to walk through. “Thank you.” As she walks past, I try to have a look at her bum, but it’s hidden by her baggy jumper, to my annoyance.
“You have a nice house,” she says, looking around. Friends say my house is empty; it’s not, it’s just that everything has its place. There is no clutter on the kitchen side.
“Thank you. Would you like a drink?” I say, walking towards the kitchen. She follows me.
“Do you have any wine?” she asks. I turn around, and there is a sparkle in her eye.
“Red or white?” I reply.
“Red, please.” She watches me as I get a glass and pour her some wine.
I hand her the glass. “Thank you.” She is studying me again as she takes a sip of the wine. “Get naked.” She commands.
I’m caught off guard. When I don’t start stripping immediately, she says it again. “I said get naked.” I start taking my clothes off, unsure where this is going. I stand there completely naked. She walks around me and whispers into my ear. “Close your eyes and don’t open them.”
I do as I’m told and close my eyes. I hear her get something from her bag and then feel her breath on my cock; it instinctively twitches.
“When was the last time you wanked?” she asks me.
“The night we first spoke,” I reply sheepishly.
“So four days ago?”
“Yes.”
I feel something cold encase my cock and balls; I take a breath in, shocked by the coldness.
I hear a click and no longer feel her breath against my cock. “Okay, you can open your eyes.” She is standing there with a wicked grin on her face.
I look down at my cock and see she has put a chastity cage on me with a padlock. I look back up at her, and she is swinging a key around her finger.
“Do you normally do this?” I ask, somewhat shocked. In my mind this wasn’t what I thought was going to happen.
“Sometimes, not that often.” Her wicked grin widens on her beautiful face. “You can do all your normal functions, but you’ll have to sit down like the sissy bitch you are to pee.”
I was shocked by the complete change of character. Then I realised this was what I was paying for; I was finally meeting Mistress Natalie. My cock wanted to grow, but trapped in the cage it wasn’t able to.
“Now I’ll decide how long you keep this on for. It might be until our session, or I might just leave it on. It all depends.”
“Depends on what?” I ask. I don’t want this cage on forever.
“Depends if you are a good boy or not. Now for the next week and a half whenever I message you I expect a reply within two minutes. Okay?”
I nod my head in acknowledgment. “If I set you a task, there will be a time limit for it to be completed.”
“Okay,” I say.
“I’m going to go now.” She walks towards me and grabs my cock in the cage. “That lovely cock really does look good in a cage.” She squats down and kisses my cock through the cage. I’ve never been so horny before in my life. My cock wanted to grow, it wanted to get hard.
Then I realised, this wasn’t going to be torture for a week and a half. But then I realised that’s what I’d paid for.
“I’ll see myself out. You can get dressed now.” I watched the beautiful Mistress Natalie walk out of my house as I stood there naked with my cock in a cage.
I look down at the cage around my cock. There is a ring around my balls and then the cock is attached to it. I try and see if I can take it off, but it’s locked in place. It was a week and a half until my session with Mistress Natalie; it shouldn’t be too hard.
It was the morning of my session with Mistress Natalie. The week and a half had been long and hard. Mistress had sent me videos of her daily, in varying costumes that she might be wearing today. She would also send me porn and tell me to watch it. A lot of it was femdom porn, ending with the man getting fucked with a strap-on.
To say I was horny was an extreme understatement; I was gagging for a release. I had done every task Mistress Natalie had sent me, usually well within the time limit.
I walked up to the house at the address Mistress had sent me and knocked the pattern I was told to knock. It opened a few seconds later.
Mistress Natalie was standing there still as beautiful as when I first saw her, she had a trench coat on which I thought was a bit unusual. She was wearing latex boots with a stiletto heel.
“Hello, my submissive sissy bitch. Are you ready to be played with?” The hint of a smirk tugs at her lips.
“You have no idea,” I tell her desperately.
“Well, come in.” She closes the door behind me. “Follow me.” I follow her through the house and then down some stairs coming into the basement.
“Take your clothes off,” she commands me, which I obediently do. “Fold them neatly and place them there.” She indicates where with a black cane.
“Come here,” she commands.
I walk to the middle of the room. She secures my hands in cuff restraints above my head and then does the same with my ankles. I watch her stand in front of me and undo the rope around the middle of the trench coat letting it fall to the floor in some swift movement.
I feel my mouth drop open; I couldn’t help it. Mistress is standing there in a black wet-look crotchless underwear set complete with wet-look stockings. Her small pink nipples are showing as well as her completely smooth pussy. I look up into her eyes; she is standing there with a massive smile.
“Do you like what you see?” she questions.
“I don’t think I’ve ever seen anything more perfect.” I feel my cock pressing against the cage desperate to grow.
“Okay, your safe word for today is Jellytotts. What’s your safe word?”
“Jellytotts,” I repeat, still mesmerised by how she looks.
“When you say the safe word we will stop doing whatever we are doing. Only use this word if there is pain, and I don’t mean ouch that hurts, I mean real pain. Understand?”
“Yes.” I make a promise to myself that no matter how much pain she causes me or how past my limit she pushes me I’m not going to say that word.
She takes a step towards me. Before I realise what’s happened I feel the cane lash into my cock. I feel tears fill my eyes from the intense pain.
“Yes, Mistress.” She points at me with the cane. “You will address me with Yes Mistress.”
“Yes, Mistress,” I repeat again.
“Good, too much use of the safe word will result in the session ending. I’m here to push you beyond your limits, if you are really going to be a little sissy bitch then I have no need with you. You are just wasting your money.”
“I understand, Mistress.”
She walks behind me. I feel her fingertips trace down my spine and rest between my arse crack, her fingertips trace down resting right on my arsehole.
“Did you like the videos I sent you?” Her fingertips pushed against my hole.
“Yes, Mistress,” I tell her.
“Did it make you horny seeing the men getting fucked up the arsehole?”
“It did, Mistress,” I tell her.
“Do you want to explore this avenue?” she asks me.
“Yes, Mistress,” I tell her, my cock is in agony.
“You understand what you are saying, yes?”
I nod. “So you want your girly boy pussy used?”
“Yes, Mistress.” I feel my cock leaking pre-cum, something that had gotten worse as the week went on.
I look down, which causes Mistress Natalie to look down as well.
“You’re making my floor dirty.”
“I can’t help it, Mistress. I’m so horny,” I plead with her.
“I don’t need excuses. How are you going to clean it up?”
I look around the room for any tissue. “I don’t know, Mistress.”
“Wrong answer.” I feel the same lash at the back of my legs. I can’t help but yelp in pain.
“I’m going to untie you and you will use your mouth to clean up the mess you’ve made.”
I stare at her in disbelief.
“Is there a problem?” she asks menacingly.
“No, Mistress.”
She unties me and nods at the floor. I get down onto my hands and knees. I hesitate for a second, and I feel the cane whip my arse. Not wanting a second whip, I begin to slurp up my pre cum off the floor. I feel utterly humiliated. I can feel my cock trying to grow inside its cage.
I then feel the tip of the cane pressing against my arsehole. Having finished cleaning up, I don’t move.
“Good boy,” she praises me. “Stand.”
I stand up, awaiting instructions.
“I bet your cock must be aching so much.” It isn’t a question. She runs her finger between two of the metal bars; her touch almost makes me cum. My cock starts to leak pre-cum again. “Better clean that back up again.”
I get back down on my hands and knees and lick up my pre-cum. While I’m doing it, I feel Mistress Natalie take hold of my swollen nuts and begin to play with them. She squeezes them softly and then hard, pulls them away from me, and I groan in pleasure.
“You aren’t allowed to cum,” she tells me while squeezing my balls so hard I yelp.
“Yes, Mistress.”
“You need to be vocal, if you are going to cum, tell me.” She caresses my balls more. I can feel the pleasure building.
“I’m going to cum, Mistress,” I tell her.
She stops caressing my balls and instead slaps them, instantly killing the building orgasm. I groan in pain and disappointment. She chuckles.
“You are nowhere near close to cumming yet, cutie.” I watch her walk over to a glass cupboard and take something out. Her arse looks incredible, it’s the kind of arse you only get from working out.
When she walks back towards me, I can’t stop looking at her pussy. Something she notices.
“Do you like the look of my pussy?” she asks, standing right in front of me. Her pussy inches from my face.
“Yes, Mistress, it looks amazing,” I tell her.
“Maybe if you are good, you can eat me out.” She leans forward and places a collar around my neck.
She pulls on the collar with the chain attached to it. “Come, it’s time for your walk.”
She proceeds to dog walk me around the dungeon. If at all, my cock leaks pre-cum, which seemed to be nonstop, she makes me lick it up.
“So have you ever shoved anything up your boy pussy?” Mistress Natalie asks me.
“An ex used to put a finger on me while blowing me sometimes,” I tell her.
“Did she ever give you a prostate massage?” she enquires.
“No,” I reply.
“Well, that will change.” My cock is agony now; it aches so much. I have never been this horny in my life. “Face on the floor and keep your eyes closed.”
I hear her heels clicking on the floor, but have no idea what she is doing. I hear her walk back and behind me. I feel her coat my arse in something wet, which I assume to be lube.
“Relax for me,” she commands. I feel her finger press up against my arsehole and then slide inside me. I can’t help but moan.
“This right here.” I feel her press on something, almost behind the base of my cock. “This is your prostate.” She starts to massage it, and it feels amazing.
“I’m going to cum,” I warn her. Her finger slips out my arse and she slaps my balls. I groan.
I feel something cold and hard press up against my arsehole. The pressure builds until something pops into me. I moan in pleasure. This feels bigger than her finger.
“This is a butt plug, we need to get that sissy hole nice and stretched.” She walks around in front of me wearing a strap-on dildo with a huge, thick dildo attached.
“Open your mouth,” she commands, and I obediently open it. She puts the tip into my mouth and tells me to suck it.
“This twelve-inch dildo will be going up your arse by the time I’m done with you. I’m going to fuck you so good and make you cum so hard that you’ll turn into a bottom slut.” I look up at her, the dildo in my mouth and a mischievous grin on her face.
“You look so cute with my cock in your mouth.”
