What's a Sissy to Do?

The following story is a fictional re-imagining of a situation I found myself in. At this moment, I have no real plans to make it into a series like some of my previous work. It's loosely based on true relationships that I've had with some likeminded people over the years, but it is nonetheless fictional. Anyway, I think that's enough from me, on to the story.

We've been messaging informally online for a couple of months now. It's the longest that I've ever chatted with a prospective daddy ever. Before we even started messaging, we had a back and forth email thread that went on for about 3-4 months. That means I've been communicating with this man for 5-6 months total. Technically speaking, that's longer than any relationship I've ever been in.

Not for a lack of trying of course. I've just never been able to truly commit. This behavior isn't limited to relationships. I have a hard time committing to anything. I'm always changing the wallpaper on my computers and phone, I change up my everyday style all the time, enrolled in school only to drop-out a short way in, and it the list goes on and on. I'm telling you this so that you can understand just how impressive it is for me to carry-on conversation with this man for close to half a year.

I haven't even met him. I've only seen pictures of his body. For all I know, they aren't even pictures of him or they're outdated and not an accurate representation of what he looks like. He claims to be over the age of 40 with a family of his own. He has a career in education, but won't provide further details as I've asked that we keep private about our personal lives. He's caucasian with a bit of hair on his chest and not much of it anywhere else. His crotch is clean shaven. The cock itself looks to be about 4-5 inches in length when soft. Unlike other men that I've interacted with online, he has not sent me any photos of what his cock looks like fully erect. He says that he wants to leave it to my imagination until we can meet in person so that he can see the look on my face when he reveals the full size to me. He's also very well written, something that I really enjoy.

I first came across this gentleman, who shall remain nameless because, if I'm being honest, I don't know his name, on the popular gay hookup site, Squirt. I don't consider myself to be gay, but I've struggled to find men to explore my kinks with me through other dating or hookup sites/apps. I figured I'd give it a shot and create an account to see if I'd have better luck finding some likeminded men. Once my account was created and my profile was completed to my liking, I started to get some messages. Nothing spectacular. I had very low expectations anyway.

I spent a week or so actively chatting with men on the site. Responding to messages, reaching out to some people who had interesting profiles, and browsing profiles for inspiration in general is what I spent most of my evenings doing. I had a free trial to the paid features for Squirt that was running out in a couple of days when I received a message from the man mentioned earlier.

I don't remember the initial message itself, but it included a well-written introduction of himself and what he liked about my profile. He thought that we may be compatible and decided to reach out to me to get the ball rolling.

In my response, I asked that we find an alternate communication method as I was losing interest in Squirt, but would like to continue chatting with him. This is how our email thread began.

In the email thread, I told him that I don't really have an attraction to men, which is why I don't consider myself to be gay, but I do have an attraction to being made to feel sexually inferior by a man. I then elaborated on this by telling him I get turned on when I think about being forcefully taken and used for another man's sexual pleasure. He seemed to be interested in these things that I shared with him.

He told me that he wanted to establish a mutual understanding between the two of us. He wanted to come to an arrangement that would benefit the both of us. In order to do this, he said that he'd be interested in helping my explore some of my kinks, but in return he wanted to take charge. This meant that he wanted me to tell him all about my sexual fantasies and desires. He wanted to know what turned me on, what I jerked off to, what I have experience doing, and what I think I might enjoy. From here, he said that he'd use this information to formulate a plan for what our first encounter would include.

I really appreciated this approach. This is the first time that I've ever had such an in-depth conversation with a potential daddy. In my past experience, we'd just exchange some pics, set the minimum limits and we'd meet. We wouldn't chat after it was all said and done. They'd use me and then they'd leave. That'd be fine if the encounter we had lived up to any of my expectations, but they didn't. Because of this, I haven't bothered to put any effort into exploring this kink.

He was different though. He was definitely interested in fucking me, that's for sure, but he also expressed an interest in having control over someone like me that he could use to relieve himself of stress. He liked to take on the role of an authoritative figure. He wanted someone that he could mould into his own. The conditions that he set out for me for our eventual first meeting are that when I arrive I'm to strip naked once the door is closed. I will leave my belongings at the door, place my hands at my side, and stand still for his inspection. Prior to the meeting, I'm not to shave at all. He wants to get a good look at me before any alterations to my appearance are made. My body is to be his canvas.

The only other piece of information he's given me at this point in our conversation is that once I present myself to me, he will signal the start of our session by tying a pink bow around my cock and balls. This will effectively act as my collar. I am to wear it at all times when in his presence. I will not be allowed to touch it. We'll start every session the exact same way. I will present myself, nude, and he will tie the bow around me.

The way that he got his point across really turned me on. I responded to him by divulging all of my dirty secrets. I loved the fact that a complete stranger, knew all about my naughty kinks. I told him how much I love the idea of consensual non-consent. I wanted to meet a man that, upon inspection, would deem me to be unworthy of presenting as a man when with him. I wanted to see what it would be like to have him pick out my outfit for me, to dress me in what he wanted to see me in. With this as the driving force behind all of my fantasies, I told him about how I'd like to be trained and broken in by a man against my will. I wanted him to train me to physically enjoy having his cock up my ass even though mentally I know it's not what a man who presents as straight would enjoy.

My biggest fantasy is to be made to cum while a man is deep inside of me. Heavy emphasis on the word, made. In this fantasy, I'll be dressed in slutty lingerie. My thong will be pulled to the side because my daddy can't be bothered with waiting for me to take it off. I'll have on a wig, no preference for the style, and I'll be wearing a bra. I'll be in high heel stilettos of course. They're my absolute favorite part of the outfit.

Walking in heels is a challenge. They change a person's gait, forcing them to take shorter steps and sway their hips in a feminine fashion. On me, they make my legs look great and help frame my ass quite nicely, but I can say with confidence that I cannot walk in high heels. This is part of the attraction I have to them. When I'm wearing high heels, I'm at a physical disadvantage. I can't walk as quickly, I can't run at all, and most importantly I cannot firmly plant my feet into the ground and make a stand to defend myself. Knowing this makes me feel vulnerable.

In my fantasies, I'm always in high heels. I won't be able to physically resist a man when I'm wearing high heels. I'll be at his mercy. This is key to me because if I can't resist physically, I can only try and resist mentally.

So, back to being made to cum with a cock inside me. Once I'm all dressed and ready, it's time to take care of daddy. Seeing me dressed will turn him on and he'll no doubt want to relieve himself. Knowing that I can do nothing to deny him physically, I'll resign myself to submitting. In my head, I'll be thinking that the faster he cums, the better. It'll be over once he's gotten his rocks off. It'll hurt physically, but the pain won't compare to the humiliation I begin to feel when I start to feel myself needing to cum. I fantasize about having my body betray me. How can I look him in the face and say I didn't enjoy it when the proof just shot straight out of me. I'll have been broken in both physically and mentally, and only then will I know what it's like to be owned by a man.

After sharing all of this with him, I got no response for a few days. I thought that he lost interest or maybe just wanted me to write out some fantasies for him to jerk off to. I was fine with this result actually. I got to jerk off to my fantasies and knowing that another strange man on the internet knows I'm secretly a sissy and I wouldn't have to commit to actually meeting him. This was great.

What happened next wasn't so great or so I thought.

He responded.

His response was written as an example of a potential scenario that would happen in our first meeting. He said that he responded this way because he wanted to see my genuine reaction to our first meeting without it being spoiled ahead of time. He didn't want my imagination setting an unrealistic expectation. He even went so far as to follow-up his response by providing an alternate scenario for our first meeting. Since then, we've discussed more potential scenarios as we've continued to learn about each other's fantasies.

Initially, I didn't know how to feel about his response. I tried not responding and just forgetting about him. We weren't really too invested in one another anyway. No personal info was exchanged and we never shared any face pictures. I tried to tell myself that I only chatted with him so that I could have an audience for some written exhibitionism. I got what I wanted when I masturbated to the dialogue of the conversation. End of story.

This didn't work.

I found myself re-reading the different scenarios he mapped out for me. I couldn't stop myself. I needed more. I had to respond.

That's how I found myself stuck in this current situation. I can't get enough. No matter how hard I try, I keep coming back to him. I can't stop myself from responding to him. It seems to be a combination of his imagination and the way he presents it. It's almost as if he's painting a picture for me. The scenarios he describes practically play out like movies in my head. It's absolutely intoxicating.

I've re-read the entirety of the conversation numerous times now. I've even picked out my favorite bits and pieces from each one to start to formulate scenarios of my own based on his ideas. The best part is that nothing he's suggested is unappealing to me. Everything he's included in the scenarios falls within something I've previously mentioned wanting to explore. He's just put his own spin on it.

The ideal meeting in my fantasy would pick up right where he left off previously. To refresh your memory, I'm standing just inside his front door completely naked and he's just finished tying a little pink bow around my cock and balls. The rest of the fantasy goes like this:

He'll then explain to me that when this piece of ribbon is on me, I am to refer to him as Master. What I previously referred to as my cock and balls is now just my sissy clit. When he's explaining this, he'll have my sissy clit wrapped in the palm of his hand. He points out that I look absolutely tiny in his hand. Instinctively, I'll look down to see that he's telling the truth.

This is when the inspection would begin. I'm told to spin around so that my back is now facing him. I'm shocked to feel him squeeze and firmly grip my hips. Involuntarily, I let out a bit of a moan. I'm deeply embarrassed by this and can feel myself start to blush.

"Could be slimmer, but these are some nice hips. I can get a good grip when I take you like this" is what I imagine him saying in this scenario. He hasn't added any details to explain his inspection process, so I fill in the reasons with my imagination.

Next up on his inspection list will be my butt. He wants to get a good feel for what he's dealing with. Now, he prefers the feeling of a smooth butt, but has specifically asked me not to shave before this meeting.

He'll place both hands on me. One on each cheek and get a nice firm handful of me. He'll then make me spread my feet apart and hold my cheeks open for him so he can get a good look at my hole.

He then places a hand on my shoulder and turns me to face him again. He puts both hands on my shoulders and gently pushes me down to my knees. Once I'm kneeling, he places a hand on the back of my head and lightly pulls me toward his crotch, stopping with my nose inches away from him. Then he places both hands on my head, one on each side, by my ears and just holds me there.

He kisses his teeth.

I look up to see him shaking his head. He looks a bit disappointed.

"As the first lesson in your training, you're going to learn how a proper sissy boy kneels" he says.

"What?" is my response.

"Did I tell you to speak?" he says as he lightly slaps my cheek.

"No... master" is my reply as I fear a more forceful slap.

"When you learn how to kneel to my satisfaction, we'll then take you to the bathroom so that I can shave you. Once you're nice and smooth, you'll get your first chance to thank me" he'll say with a smirk.

He'll then nitpick at the way I'm kneeled. On my knees, but much to defiant. He wants me more relaxed and submissive, so he points out that when on my knees, I should do my best to have the heels of my feet under my butt. My hands are to be in my lap and I should lean forward a little bit towards his crotch so he can get a good view of my butt behind me from where he's standing above me. I should also tilt my head upwards so that I can look up at him. This way it'll be clear who's in charge.

Once I've mastered this position for him, he'll make me crawl into the bathroom behind him. I'll then get into his bathtub but only my lower half will remain in the tub. I'm to kneel inside the tub with my ass up as I lean over the side of his tub. He then steps into the tub behind me and proceeds to shave my entire backside.

I've never been shaved by anybody else, but I imagine it'll feel very erotic and foreign. I'll admit, I sometimes get turned on when I shave my own sensitive parts.

When he's done, he'll dry me off and then order me to follow him out into his living room where I'll find my outfit for the session neatly laid out on his coffee table.

I don't need him to tell me what comes next. I reluctantly reach for the items, but he stops me.

"What do you say?" he sternly asks while tapping his foot on the floor.

"Thank you, Master" I quickly reply.

In my fantasy, I naively think this is what he meant when he said I'll have my first chance to thank him. This is not the case at all.

He steps forward toward me so that we're standing face-to-face.

"There's no backing out now. We're already half an hour into this meeting, we're going to do everything that I have planned" he says to my surprise.

I'm a little confused, but before I can ask him what he means by this, he'll force me to my knees again before he starts undressing.

I don't say a word while he gets naked in front of me. I couldn't even if I wanted to. There are no words that can describe the way I feel as reality sets in. I'm on my knees in front of another man. I have a pink ribbon tied around what I'm now calling my sisst clit. The man has just finished shaving my ass so that the can use it as his fuck hole later on, and now I'm staring right at his smooth flaccid cock.

His cock is soft, but it's about the same size as me when I'm fully erect.

He'll start to speak, but I won't hear him. I'm too fixated on the scene that's unfolded right before my eyes.

He'll raise his voice and he begins to lose patience with me.

His hand will go to his cock as he grabs hold of himself and points the slit in my direction.

"I don't know if I can do this" I'll meekly squeak out.

It won't matter. I'm in too deep. It's too late. I know what he'll say, there's nothing I can do now.

"I didn't clear my schedule for you to be a little tease baby" he says to me as he continues to point his cock at me.

"I know, I'm so sorry, I feel so bad. Maybe we can try this again another time, this is all a bit too much for me. It's moving faster than I thought it would. I don't think I can go through with this" I say.

"We talked about this. I knew you'd say this. I told you that as your Master, I would train you to go past these fears. How else are you going to explore?" he asks.

He takes another step towards me.

I'm still frozen there on my knees. My smooth bare behind resting on my heels, hands in my lap just like he taught me.

I don't even realize.

"Look at you, you're already making progress. You're right where you belong. We can slow things down. I know it's cliche, but how about we start with just the tip?" is what I imagine him saying to calm me down.

He'll see the confusion on my face. He knows that my inner self is trying to resist.

He takes another step forward.

My head tilts back and looks up at him.

Another step and he's now right in front of me. His hand holding his growing cock. He's excited by how this has played out. Seeing his prey in front him is getting his blood flowing.

I'm still frozen there. It feels as if my body is paralyzed. Only my eyes are moving. I close them for just a brief second. Maybe this is just a dream and when I open my eyes this will all be over. I'll wake up in bed with my laptop on and our conversation open in front of me.

It's not to be.

As I open my eyes, I see that he's taken another step forward and his ball sack is hovering over my chin as I look up at him. It's as if I can feel the heat emanating from the tip of his cock over my forehead. He's that close.

I get a good whiff of his musk as I take a deep breathe through my nose. Afraid to open my mouth. Afraid that if I do, his balls might drop right in.

He takes his hand off his cock.

For a split second, there's silence.

It feels like an eternity has passed as I'm stuck in a trance, but in reality it's just mere seconds.

When I finally snap out of it and understand what's going on, it's too late.

My eyes are darting around trying to get a sense of the room and my mind is racing trying to process what the fuck just happened.

It's hot.

The feeling of his shaft resting on my face.

He gyrates his hips a bit causing his cock to rub on my face. I try to lean back and get away, but I feel his hand on the back of my head just like in the inspection.

My eyes widen a bit as I make the connection.

With his free hand, he takes hold of his cock again and begins to lift it off my face and then let it drop on me again. He repeats this a couple times until I no longer try to lean away.

There were no words exchanged between us, but we both knew what just happened. I stopped resisting. I've resigned myself to the path of least resistance.

I'm hoping that maybe he'll cum quickly and I can get the fuck out of here. I agreed to this, and I would hate to have been strung along if I were in his position. I just need to get through this one meeting.