Sissy Masochist

I'm writing this because, personally, I really enjoy writing about my sexual desires and turn ons. I find it very taboo to express these secret thoughts for strangers on the internet to see, and to be completely honest, I have a massive hard on as I write this. Well, not massive, quite the opposite actually, but you get the point.

Reflecting on my previous encounters, dates, relationships (if you want to call them that) I've come to realize just what really gets my blood flowing. I've found common themes between these real life experiences and the porn that I watch and the stories that I read. These themes are that I love sexual experiences contrary to my regular everyday life.

From 9-to-5 I'm just another regular straight guy. A man's man of sorts. I am in control of my work life, although I'm not a manager or a boss by any means. I like to go to the gym and stay fit and in-shape. I like sports and video games. Behind close doors though, I don't want to be in control. I like to think that I am in control. To think that I'm the man, the alpha. Even though I knowingly and willingly agreed to meet another man who's usually just as manly, just as fit and in-shape, and just as in control as I am.

The difference is that once we're in a room together, he's the real deal. He's actually manly, he's actually alpha, he's actually in control. He wastes no time letting me know that he sees right through me. I like resisting his insults and attempt to humiliate me. I stand up for myself and put my foot down, but it's no use. It's futile. One way or another, the man finds a way to overpower me. Ways that he does this is by telling me that a real man would never have agreed to meeting him in the first place causing doubt to start creeping into my mind. I try to justify it by saying that I'm just exploring, but he continues to push me, and eventually it leads to the two of us comparing the size of our manhood. This is what I like to think of as the first domino falling.

When it's time to reveal ourselves and we're both naked it becomes very clear that I am the smaller man. This brings me great shame, but only validates the mans thoughts and statements. I'll still try to resist, but the man opposite me can see my weakness. He didn't plan to meet me and waste his time. He has sexual desires that need to be taken care of. Pent up sexual frustration. He came to get some ass. This is usually when they push on me harder.

In the past, I've had a man tell me that since I'm already naked, I might as well do at least one thing that I met him to do. See what my ass looks like in a thong. He then passed me a tiny pink thong. We had a brief back and forth, but he eventually convinced me to put it on. One thing lead to another, and I found myself wearing the thong, some thigh high stockings, and a pair of strappy black high heels. I've also had a man take a more forceful approach. He told me that he had the larger cock, and that because of that, he was going to dictate the rest of the night was gonna go, and I better do what he says or get out. At the time, I don't know why I stayed, but I did. I got dressed, and within 30 minutes I found myself on all fours on his bed while he pounding me.

I love the idea that the man was able to get what he wanted from me one way or the other. Slowly but surely, he was able to manipulate me into my own humiliation. My favourite part of having them dress me up is when they get me to put on the heels. I can't walk in heels whatsoever because every time I've ever worn heels, I didn't spend much time on my feet. This means that even if I muster up the strength to resist, I can't get away in heels. It's as if I'm sealing my fate.

Once dressed, the men pounce, both literally and figuratively. They tell me that I look good, and that I was meant to wear the outfits that they put me in. It's so embarrassing, but deep down, I really love it. They follow it up by letting me know that they didn't appreciate my earlier resistance, and that if I actually were a real man, I wouldn't be the one dressed like a slut. From here, the night really is out of my control. In my mind, I'm no longer a man. All the evidence points to me being the beta to his alpha. After all, I am dressed for the part.

I refute their claims and continue to push back, but at this point I know it's no good. I tell them that I tried it, I dressed up and I don't like it. I tell them that I'd like to go back to my male clothes and that I'm leaving, but, like we agreed earlier, they don't accept this answer from me. They say that after watching my get dressed they're too turned on. The proof is waving itself in front of me. They're erect and it puts me to shame. At this point, I usually bow my head in submission and the tone in my voice changes. It goes from being resistant and defiant to being meek and submissive. I change tactics and try to beg them to let me change back.

At this point, I love nothing more than for them to get aggressive. I like for them to assert their dominance over me. To put the nail in the coffin. They tell me what I'm going to do instead of what I want to do. Examples of this are usually me being told that I'm going to get on the bed, or on my knees, or bend over the desk, and that they're going to show me how a real man handles defiance from his sissy. Then we get physical. Like I said earlier, I try to get away, but because I can't walk in heels, I easily get overpowered. Within my first few steps, the men are easily able to grab me and make me get into the position that he demanded me to get in earlier.

My favourite was when the man let me get a step passed him before he grabbed me by the back of my neck and forced me to bend at the waist over his bed. I was in a nightie, black stockings, a g-string, a pair of crimson red fuck me pumps. He then pinned me down with his weight and began to tell me straight into my ear that this was the last straw. He's going to take what's his and that I was going to like it. I was so turned on. I saw the light of day, I was passed him and my pile of clothes was within reach before he snatched it away from me. He broke me. He let me go, but I didn't dare move a muscle. He got a condom and the lube, pulled aside my g-string and prepped me. Before entering me and making me his bitch, he told me right in my ear again, that I didn't move because deep down, I knew that I belonged there with my ass ready to be torn up by him. All throughout the night as he ravaged me, he didn't miss any opportunity to let me know who's in charge.

"What were you saying about being a man?"

"How manly does my cock feel inside you?"

"Do you like being my bitch?"

"From up here, you feel as tight as any bitch I've ever fucked?"

"Next time, you won't waste my time, and you'll get dressed as soon as you enter the room."

"I love the way your ass jiggles while I fuck it."

While all this is happening, I'm clenching my teeth, biting the pillow, holding my breath, and overall just trying my best to keep quiet. Praying it will all be over, but...

"Uhhhh" escapes my lips.

"There it is. I knew you'd love this big, manly dick inside your sissy ass" the man says.

This is the apex of my desires. He's managed to, against my will, make my body betray my mind. My body let it be known that it enjoys his dick, but my mind is telling me not to. It's too humiliating to process. Why did I moan? Why couldn't I stop myself? Why did I just give in this man? I gave him the satisfaction of knowing that he's right. He proved me wrong. Proved that for that night, I'm not the man.

I'm humiliated knowing that I'm being broken by another man.

I'm embarrassed that he was able to prove that he was my superior.

I'm emasculated knowing that I'm in the feminine, submissive role.

Reality then sets in.

I'm erect knowing that I'm his sissy.