Sissy Sex Dungeon

Disclaimer: I’m going to start this story right where everything gets going without much of a set up, and I plan on telling it as the experience it was for me. A lot of parts in the story will seem like kidnapping, forced sex, or even borderline torture. I assure you that the weekend itself was planned(though I wasn’t sure what all specifics would take place) and at any minute I could have left or taken a break. Also I was 24 at the time, so this isn’t a case of someone being taken advantage of at the age of 18 or anything. On the flip side the other party was allowed to call it off if they felt uncomfortable with the scenario at any point, or if I got aggressively defensive making them feel threatened. The point of the whole weekend was just a long roleplay of me getting held prisoner and used as a sex slave basically. Let this also be a trigger warning for anyone who doesn’t want to hear about this type of stuff. As I said above, I’m going to tell this as the experience that was intended, and won’t be talking about roleplay or it not being real from here on out. Now that that’s out of the way, here we go…

I began to stir from sleep as the sun finally began peaking through the window, though I wish it would have taken its time, because I couldn’t remember the last time I slept so well. I’m not sure if it was the feats of a dinner from the night before, or this amazingly comfortable bed that I’m not financially well off to even guess at the material. Whatever was the reason, that was one of the deepest slumbers I’ve ever experienced. Seeing as I’m already awake I better go find the owner of the house and thank him for the hospitality, and then slip out before I start hearing talk of a presentation, or time share, or whatever it is that I’m sure he’s selling.

Or that’s what I’d like to do at least, but as soon as I made to leave the bed, I realized I had a problem. My arms and legs were tied to each corner of the bed just enough so I was restricted from any real movement. I quickly began scanning the room, which even through my stress I couldn’t help but notice how nice the room was, from ceiling to floor and all the furnishing in between.

Then a voice cut through the air so suddenly that if it wasn’t for the restraints, I would have launched myself off the bed for sure. “So, you decided to finally wake up huh?”

It was the owner of the house. If I had to guess, I’d say he was in his 40s, and he clearly didn’t live a sedentary lifestyle. I wouldn’t call him ripped or muscular, but he was definitely in shape and had plenty of energy about him. He had a naturally authoritative voice, the kind that could immediately gather attention in a business setting whether they were a key speaker or not. As he stood and approached the bed, there was an almost hungry aura about him that made his average height feel significantly taller.

“So uhhh, what’s goin on here?” I was trying to play it off casually as if this was a normal type of prank to play on someone, but something felt terribly off. “Did the rest of the guests also wake up strapped to their bed?” I offered a pitiful laugh, that was met with a smile that did not feel like a comedic joking smile.

“Everyone else is gone. It’s just you and me. Why do you think you’re still here and not anyone else?” I generally get along with most people and rarely have conflicts, but I know a threat when I hear one.

“Did…did I win the golf club giveaway?”

He just pointed at the light fixture on ceiling, “That’s a camera in there, and I saw what you did.”

I froze. This was one of the most embarrassing moments of my life. I’m openly bisexual, and generally I go for girls most of the time, but secretly I love being a sissy. Something about wearing the girly clothes and feeling like a pretty little slut is just so fulfilling. I own a handful of outfits and lingerie, but rarely buy new ones since I’m so secretive about that part of my life. So I’ve developed a bad habit of trying on clothing(never stealing or taking them) I come across if the moment allows, which I thought staying in a fancy room by myself would never go noticed.

“I..I..I’m so so sorry. This is so embarrassing and I don’t even know how to begin apologizing. I’m not sure what family member or friend those belonged to, but me touch them was very out of line.”

He sat down on the edge of the bed, and I instinctively tried to pull away, but was quickly reminded of the first predicament of the morning, and only managed to squirm.

“It’s nothing to worry about, I’ve already thought of a way you can make it up to me.”

Inside my head I breathed a sigh of relief. Everything seemed to be going smoothly. Tying me to the bed to make sure I didn’t leave before he could approach me about this seemed a little overkill, but rich people can be eccentric I guess. But the smile still on his face wasn’t one of a person that’s about to give you good news.

He stood up and began pacing the room. “Forgive me for monitoring you without your knowledge, I just never can bring myself to not get suspicious of guests that are over. Makes you wonder why I even have any at all doesn’t it?” I tried to respond but he continued on with even looking at me. “But it seems I have justifiable reasons this time doesn’t it? I’ve been thinking about what I should do with you, and this invasion of my privacy in my own home. You’re a closet sissy aren’t you?”

The question took me so off guard, as I rarely expect your average person to even know why a sissy is, let alone accuse me of being one just for wearing clothing(even though there’s be accurate). All I could do was stammer but he wasn’t done yet and continued on.

“I could tell by the way you were checking yourself out in the mirror, decked out in my ex wife’s clothing, that you felt incredibly sexy in that moment. To be honest, I’d have to agree.”

My mind literally froze. This was the last thing I expected to hear, so maybe I’m going to get off easy and he just wanted me to feel embarrassed and ashamed.

“So this is what’s going to happen next. You’re going to right the wrong that you did, by doing it again. I’m going to release you from these ropes, and you’re going to go pick out your favorite outfit from last night then model it for me. From there we can just play it by ear.” His smile no longer had an ominous air about it, now it just felt downright dangerous.

“I’m sorry sir, I didn’t mean to stick my nose where it doesn’t belong. There’s no need to push it further. I’ll just leave so you don’t have to worry about me anymore.”

“I insist.” The authority behind his words, I wasn’t sure what I should do to fix the situation. So I did what I do best, run from the problem. The second he freed me from the final restraint, I booked it. The house was bigger than I remembered, though that was probably due to the adrenaline pumping through me, but even still I managed to find the front door fairly quickly.

“You’ve got to be fucking kidding me.” The door was locked. I twisted the knobs lock, undid the deadbolt, but still it wouldn’t come open. There was a bay window nearby that I could probably smash, but as soon as I turned around my heart sank. There he was standing right behind me. I barely had time to think, how did he get behind me so quickly and quietly, before I was pushed rather hardly(I’d even venture to say borderline slammed) against the wall.

“So you want to do this the hard way then.” I tried dashing to the side but his hand was around my throat in an instance, and I was definitely right about him being in shape, I couldn’t move at all. “Come on lest talk.” He moved his hand onto the back of my neck and began guiding me back into the depths of the house. We passed through the dining room that I and the other guests had eaten in, and then immediately took a left into a small little alcove that I didn’t even notice the night before. He opened the singular door here, and revealed steps leading down. I didn’t like this at all and tried to back up, but I couldn’t fight against him at all and found myself continuing forward.

It was obvious by now that something terrible was about to happen to me. I thought maybe he was going to kill me to be honest. But as soon as we descended the final step, I realized what was about to happen and began panicking immediately. When we hit the ground floor he hand left my neck for a split second, and before a could even turn around, I felt something cold on my neck and heard a click. Then another click, as he flicked the lights revealing the entire room. Being a lifetime nerd, upon seeing the walls and general aesthetic down here, my first thought was dungeon. Then after taking another glance at the various objects and furnishing in here, that thought changed to sex dungeon.

It dawned on me that I was no longer being held and he had actually walked away from me deeper into the room. I turned to try running again, but gave up after almost the first step when I heard a familiar jingling clanging sound. Turning around I realized the cold feeling and first click I heard was a metal collar and chain leash that I was now wearing and was attached to the nearest column in the room. I wouldn’t have been able to take more than another step or two before choking myself out from the metal band now on my neck anyways. I turned back around to see him standing in the middle of the room staring back at me.

“We could have done this in a more calm way if you’d have just cooperated, but alas you didn’t listen and just had to run. Here’s what’s going to happen next. Since you wanted to play dress up, thats exactly what you’re going to do. From this moment on I own you. You exist to serve my needs and desires. I’m going to use you as my personal fuck toy, and turn you into the perfect little sissy sex slave. If you resist or don’t cooperate in any other way, you’ll be punished for it, so I suggest learning to accept your new situation as fast as you can. The only time you will speak is if I ask you a question, or if it’s related to serving me, which we’ll get to that soon enough. Your attitude is expected to be doing anything you can to please me. Lastly, from now on you will always call me Sir or Daddy. You understand all that?”

This couldn’t be real. No way this is happening to me right now. “Hold on a second there now way I’m going to let you do this. You don’t just get away with something lik-” I was cut off by a sharp slap to the face.

“This is the one time I let something slide, as I’m sure this is all a shock, but never speak back to me again. You’ll still be brought good food and will have a decent place to sleep, but your new clothes you’ll be wearing are in the trunk by your new bed. I still have things to take care of for the day, so I’d highly suggest you take this time to prepare yourself to be the best crossdressing little slut you’ve ever been. When I return I expect you to be in a different outfit than the regular clothes you have on now.” He turned to leave and just before ascending the stairs turned his head for one last snide remark. “Make sure you put thought into why clothes you pick, after all, this is going to be your first time serving your new master. You want to make a good impression when I break you in.

I felt rage boil up inside me. What made me most mad about the situation, is his arrogant attitude, as if he knows he’s won and there’s nothing I can do. It didn’t take long to check the room. Even limited by the chain leash, the room wasn’t particularly big. Just a rectangular stone basement with a couple inset alcoves around the sides. There were various contraptions around the room, most of which I could probably guess there use even if I didn’t recognize it. The only thing of note I could really even reach in my current situation was the alcove that contained my new bed and trunk full of outfits.

I didn’t plan on fully cooperating, and was going to escape the first chance I could, but why make things harder than they have to be for no reason.(if I’m being honest, I was also kinda curious to see what new clothes I had). It didn’t take more than a moment or two to realize everything in here was some sort of lingerie. If I’m expected to live in this cold dungeon of a room, the least he could do is give me sissy clothes that actually resemble real clothing. Letting out a big sigh I started rummaging through the box to find something to wear.

Probably the least revealing thing in here was a hot pink onsie type outfit. Of course there was no legging part and it barely covered my shoulders. But it was surprisingly comfortable, and I couldn’t help but notice that it rose along my cheeks nicely and made my butt look pretty good. Along the left and right side of my neck the fabric continued up from the shoulders making a collar that I buttoned, and then managed to slide the pink fabric underneath the metal collar already on my neck. I also found a pair of matching pink thigh high socks, and even a pink leather garter set that snuggly fit my thighs. I’m not sure why I decided to add the garters as well, as that only really benefits Him, but I can’t help liking dressing cute if it’s an option.

Even though it had probably only been an hour or two at most since I woke up, I layed down anyways and tried to sleep. I’m not sure if I even slept, or just stared off into nothing for eternity, but eventually I heard the noise I’d been dreading. The main door had opened, meaning he was back, and my hell was about to begin.

“Come slave!” As he beckoned for me to go over to him.

I just continued to stare at him. Does he really expect me to just go along with any of this? But apparently patience is not one of his things, because almost as fast as he called for me, he then grabbed the chain leash and started pulling me in. I stumbled and fell to the ground while he continued to drag me across the floor, until I was just a few feet from him.

“Whenever I order you to do anything, there should be no hesitation. I want to hear a yes sir, or a thank you daddy, or anything else that I’ve allowed you to say. And there better not be any attitude when you hop to it either.”

I mumbled a very angry “yes sir” in response, which I knew wasn’t going to fly, but fuck this guy. He doesn’t deserve jack.

“You really are just trying to make this as difficult as possible for yourself. Well sissy, come show me how good of a fuck toy you can be.”

With that he undid his pants and pulled his already rock hard cock out. I hate to admit it, but it was near perfect, what you’d expect to see in a high end porn. Perfect shape and big but not to big (I’d guess it was roughly 7 inches). The most intimidating part though, was how much girth it had. It wasn’t so thick that it looked fat or unproportioned, but it was big enough to instantly make me question if I’d be able to take it all. In any other situation I’d have been excited, although still nervous, to serve it. But I wanted nothing to do with this.

As soon as he realized I wasn’t going to crawl over, the chain started pulling me again. This time I was ready however, and grabbed it and pulled back on it. Unfortunately this asshole was stronger than me and while I was only scooting inches now, it wasn’t stopping the inevitable. Even when at his waist, I did all I could to hold my head back away from him.

“I’m not sure if you don’t think I’m serious, or you just really want to be punished that bad, but you’re just delaying the inevitable.” He pulled up on the leash forcing my head up against his crotch. I begrudgingly stuck my tongue out and barely licked the tip. “Come on we both know you can do better than that.” After another internal sigh, I closed my eyes so as to maybe pretend I was somewhere else, and opened my mouth.

Before I could actually start however, he stopped me one last time. “Aren’t you going to thank me for letting you taste the thing that owns you? Eventually you’re going to be begging to suck it.” I replied with the “thank you daddy.” I wouldn’t say it sounded happy but I wasn’t about to give him more attitude right before he turns my throat into his own pocket pussy.

Once I closed my eyes and went to work, it was surprisingly easy to just pretend this was a different situation, because it’s not like I’m entirely new to this or anything. At the same time, I got annoyed with myself every time I realized I was kind of enjoying it because of that. But I just couldn’t ignore the fact that his cock was so amazing. I could feel it’s size against my tongue, barely able to wrap it halfway around, as I dragged it along his thick shaft. My tongue danced back and forth, over and under, up and down, until his cock was drenched in saliva. I finally moved up to the perfectly shaped head and wrapped my lips around the tip and slid them forward until his helmet was fully in my mouth. I really began to understand how much girth this horrible man was packing, as my lips were almost stretched to their limit, and my mouth felt completely full as I slide partway down his cock. I wanted this to be over with ASAP, so I sucked away, occasionally going back to licking the length of his shaft, trying to please him so as not to endure any type of punishment.

I went non stop for what had to be at least a half hour, and it wasn’t until I finally heard a moan that I realized it had been silent the entire time while he looked down and watched me. I felt hands grab my hair and pull me back to look upwards. “Now was that so bad? You looked like you were even enjoying it.”

“Yes sir, thank you sir.” I was in no way thankful, but I was ready to be done and rest my jaw. I went to put my weight down against my legs, and immediately his grip tightened on my hair.

“You don’t think you’re done do you? You actually did a great job for the most part, but remember you’re my personal sex slave now. I know it’s big and filled up your mouth real quick, but you didn’t even try swallowing the whole thing. Will it be uncomfortable? Probably. But your purpose in life now is taking care of your new owner no matter what it takes.”

Even if I wanted to resist, he gave me no time, I barely even stuck my tongue out in time. Instantly my lips were spread open again, followed by my mouth filling up as his massive cock made its way further and further. I tried pushing back against his legs in an attempt to slowly work my way down his shaft, but quickly let my hands fall to my sides in defeat. His grip on the back of my head hadn’t loosened a bit, and he was now in control. Without hesitation he steadily slid his cock down my throat, until my face was pressed against his waist.

Never in my life had I tried sucking a cock this size, let alone attempt to swallow it. I could feel every bit of him as he filled me up, my throat squeezing tight against his cock. Part of me was kind of worried my throat would tear with how full it felt. I could barely breath and felt myself begin to panic as I was still powerless to pull away.

After a deep moan of obvious pleasure from him, I could feel him pulling out. Looking down at me “that felt great didn’t it?”

Partially because he wasn’t even all the way past my lips yet, and partially because that did not feel good at all, I didn’t even think to agree with that statement.

“I didn’t hear a response. Maybe you just weren’t sure and need another taste.” He hadn’t even fully cleared my lips before he slid all the way back in. Once again I hear him moan his stupid moan. I can’t explain it, but it has a sound of “this feels amazing, and even more so because you have no choice but to endure it.”

I’m not sure how I didn’t gag first time, but almost immediately after I found my face pressed against his body once again my reflexes kicked in and I managed to squeeze out a gag from around this monster currently inside me. Surprisingly I felt my head pulled back away from him.