Sissy Gambling Debt Pt. 03

As I was led with a leash into the large mansion owned by Lucien, I was in awe seeing how beautiful the interior was. The floor was made out of distinctive dark marble, the walls were filled with intricate artwork, and the ceiling looked similar to that of the Hagia Sophia. It looked like a place where normal guests would be expected to wear formal dresses and suits, as I wasn't the only one invited to come to their mansion. It was quite embarrassing to see everyone else there wearing fancy attire as I walked in awkwardly naked with an anal hook still lodged in my ass and smelling like piss. Lucien went off to talk to some of the guests as Chloe led me on.

As Chloe led me through the mansion, I could hear the female guests giggling and mocking me amongst themselves, saying I looked pathetic and had a tiny cock. At the same time, I could also hear the male guests whistle and catcall me as I walked by them. Some of them even groped me and smacked my ass, complimenting my appearance as cute and beautiful. This gave me mixed feelings towards what everyone was saying to me. Where I would feel intense shame amongst the women putting my appearance down, I would feel somewhat appreciated by the men in the crowd. It was a weird feeling, but I kinda liked it.

Chloe turned towards me and smiled. "You see Amber? I told you you're better off being feminized and living a life of a sissy slut. Even with your natural physique, none of the women here found you attractive, whereas some of the men complimented you." I nodded in silence as she was completely right about my appearance. I don't think I would have lasted as a man anyways with my small stature and pathetic 3 inch cock that's flaccid most of the time. The reactions here confirmed with me that women do find me ugly and unattractive.

Now that I do think about it, I've been having trouble achieving erections throughout my life at the sight of women. Even while watching straight porn, my cock only slightly gets hard and then it goes away. The feelings of sexual pleasure are fleeting when it comes to looking at women, and I've only been attracted to them because that's what society told me to be attracted to. I kept on telling myself perhaps I'm just nervous and that's why I can't get erections with women, but now I think I've just been in denial this whole time. I'm starting to reconsider my sexuality, because it felt really good when men started to compliment my natural appearance, and it turned me on a bit.

As I was reflecting on my sexuality, Chloe eventually led me downstairs to the basement. Throughout the corridors, the grandiose mansion vibes dissipated and it started to look more like a dungeon. The hallways were darker with torches being the only source of light. The walls were made up of dark colored bricks, and the floor appeared to be metallic. Eventually we approached a large medieval-looking wooden door. It had a small rectangular opening in the center that was secured with metal bars, and it had a small slit below where I'm assuming trays of food and water will be given to me.

Chloe turned towards me and smirked. "Ah, we're finally here. This will be the room you will be staying at mainly to sleep, eat, and recover." She opened the door to reveal a relatively large room with a queen sized bed, a small wardrobe, and bathroom. "I'm gonna make some things clear with you that we're keeping you here as our degraded sissy sex slave, not some regular guest that can lavishly enjoy our mansion." I nodded in silence as she explained things to me. "For the first few months, you're going to be subjected to hormone replacement therapy and at the same time conduct some sexual favors for us to make up your gambling debt. I'm leaving you with some written instruction on paper to understand your duties."

As she handed me the written instructions, she went behind me to untie the rope around my neck that was attached to the anal hook lodged in my ass. This relieved a lot of pressure in my ass, but it felt even better when she pulled out the anal hook. It made a distinctive plopping sound as she pulled it out, and my ass felt pretty gaped. She giggled a bit at the sight of my ruined asshole. "Haha! Wow, it looks pretty damaged after leaving that anal hook there for hours, I don't think your ass is going to go back to normal for a while." I moved my hand down to feel it, and it was indeed very gaped. It didn't look like it was going back to its original shape.

She then left the room and locked the door, leaving me inside by myself. I opened up the instructions to read what was in store for me. It reads as follows: 1) Throughout the day, you will be receiving some food and water mixed with experimental HRT drugs that will aid you with transitioning. These drugs come from an investment with a few doctors that we hired. As part of the agreement to become our degraded sissy sex slave, you'll be taking in these drugs as you have your daily meals.

2) There is an alarm clock under your bed. Everyday it will sound at 7:00 am sharp, and you must wake up and get ready for the day with the provided attire in the wardrobe by 8:00 am. Throughout the day you are to solely follow instructions given by us. We will have maids come into your bedroom every now and then to provide you with new attires, restock supplies, and to clean up any messes left behind from sexual favours on your end.

3) Every night at 9:00 pm and until the next day, you will be relieved of any sexual favours. During this time, you may use the bathroom on your own free will to tend to yourself. You are not to use the toilet or shower area at any other time on your own, unless given permission. If you use these at the wrong time, it will be met with severe punishment.

Those were the only instructions given to me on that paper. It seems I'll have to get used to the routine given to me as I think I'll be here for a while. Although I was originally against being further feminized, I think it's for the best. I felt so ashamed how the women viewed me earlier, and I don't think my body is meant to pleasure them. I however felt good when the group of men complimented me and gave me attention. When they groped me and smacked my ass, I had an arousal so I think I should be further feminized to attract them more.

As I was reflecting on myself, the waft of piss on my body made me have the desire to wash myself. I looked at the clock under my bed to see if I could use the bathroom, and it was indeed past 9:00 pm. I went into the shower to wash the pee off my body, and rinsed my mouth. There was however no shampoo or body wash given to me, so the smell of piss still lingered on me after the shower. As I went out of the bathroom area, I saw a metal tray of food being slid through the door. It was my first meal after a long ride to the mansion, and I was super hungry for it.

There was a large plate of squashed potatoes, carrots, bits of corn, and some whitish looking gravy on top. There was also a glass of what smelled like apple juice. I was super excited to indulge into what was provided to me. It looked like a fancy meal, and I didn't care that it was laced with experimental HRT drugs. I ate the entire plate quickly, and licked off the remnants of the sauce because I was super hungry.

Lucien stood over the door and laughed at me. "Haha, it seems you really enjoyed the food. All the male guests today helped me to create the gravy for your meal. It's our cum, and you seemed to have really enjoyed it! That drink of yours was also apple juice mixed with spurts of pee from all the ladies visiting today, including my wife's. Glad you enjoyed it slut." I was shocked that I had eaten the cum of all those men I saw today, and drank the spurts of piss from all those other women, but surprisingly the meal was delicious nonetheless.

"Thank you Lucien for the meal. You can let everyone know that I enjoyed it, and I hope there's more!" Lucien chuckled and left. I went to bed satisfied with the meal I just got despite its disgusting nature. It felt quite degrading and erotic at the same time to know there's cum from other men, and spurts of piss from other women in my digestive track. Throughout the night, I could hear my belly rumble as it digests what I just ate.

It was the following day, and the alarm clock rang exactly at 7:00 am. I opened up the wardrobe to find a woman's blond wig, pink panties, a tiny pink bra, and a skimpy pink dress. As requested by the instructions, I put on the attire and it made me look like a complete slut, the kind you'd find in an alleyway at night doing prostitution. In the wardrobe, there was also makeup with a note saying I had to put on as part of my attire. There was eyeliner, red lipstick, and pink nail polish that I had to put on.

Surprisingly for a male, I was quite good at putting on nail polish. They looked pretty good on my hands and made me look more feminine. It was the eyeliner and lipstick part that I had trouble with, and I was taking longer than expected to put this on. It was 8:00 am, which was the time I was supposed to have my attire ready by, and I still hadn't managed to put on my lipstick and eyeliner. It was then I could hear the door being unlocked, and Chloe walked in.

"You look like a stupid bimbo clown, it seems you haven't followed the instructions I've left you yesterday. The lipstick part looks terrible, and your eyeliner is way off! We're gonna have to punish you now. Bend down over the bed!" Chloe seemed pissed off, and was a bit scary. I listened to her command and bent down over the bed. She then lifted my pink dress up, and pulled down my panties. It was then she took the lipstick to write something on my back. "I'm writing the word stupid cunt on your back, because you can't follow the instructions."

She then took some lubricant and put it on my asshole. It felt cold when she rubbed it on me, and it still felt gaped from the anal hook yesterday. Although it didn't fully recover, Chloe continued to abuse my ass by shoving the lipstick and eyeliner inside. She then plugged up my ass with a large butt plug making me yelp. "You're gonna try to push out the lipstick and eyeliner the following day, and attempt to retry the makeup part you stupid bitch."

She then pulled out a whip and flogged me very hard 10 times. It made my ass bleed a bit, and I screamed every time she whipped me. The punishment was severe as my legs were trembling with pain. I should have listened to the instructions, and tried harder to put on the makeup. Lucien then came in, and pulled out an enormous dick in front of my face. Looking at it, I'd say it's about 10 inches long, and more than 3 times the size of my own cock. The girth of his dick was also much larger. My sissy cock was nothing in comparison!

"Suck my dick bitch!" Lucien grabbed my face and shoved his large dick into my mouth, deep into my throat. He went in and out slowly, and it was difficult to breathe. As he pushed his manhood deep into my mouth for several minutes, he eventually cummed in my throat. My gag reflexes kicked in, and I started to cough and spit some of his cum back out. Chloe then pushed my head down to lick off the cum I spat out, and made out with me. We exchanged Lucien's cum back and forth through our mouths, and eventually Chloe told me to swallow it.

Chloe turned to me and smiled. "We can't waste any real manly semen now can we? Your pathetic semen doesn't matter, but this one does. Remember to always swallow my husband's cum alright?" I agreed with Chloe. After they were done sexually abusing me, both of them left the room. It was still the morning, so I'm not allowed to use the bathroom until later tonight. Because I wasn't able to rinse my mouth, Lucien left a strong aftertaste of his cum in my mouth. I tried to rinse it with my own saliva, but it didn't go away. He completely loaded his cum into my mouth, and left me there like a ragdoll bitch.

Breakfast was finally served as another metal tray was slid through the door. This time, it looks like I got some scrambled eggs, toast, and milk. Looking closely at my meal, I can see someone cummed on my food again as the same whitish looking fluid was put all over the eggs. The milk also looked a bit yellowish, so I'm sure someone put in spurts of pee again. I was hungry, and despite all that disgusting cum and pee in my food, I ate it and enjoyed it nonetheless.

Throughout the day, lunch and dinner were also served in a similar fashion. For lunch, I had a ham sandwich with cum inside it, and sparkling water with spurts of pee. For dinner, I had pasta with cum on top, and wine with spurts of pee. Lucien would come into my room intermittently to make me suck his dick, and he would cum in my mouth as usual. His wife Chloie would be there to make out with me with Lucien's cum in our mouths, and she'd make sure I lick and swallow every last drop of his cum. It's something she refers to as alpha male semen.

For the next following weeks, I was subjected to similar abuse if I hadn't put on my attire correctly. Everyday, the maids would prepare different kinds of slutty attire and makeup that I had to put on. My panties and dresses would come in a variety of colors each day, and I was given all sorts of makeup to put on. Chloe punished me in different ways if I didn't put on my attire and makeup properly. This ranged from extreme flogging, burning me with cigarettes, spiting on my face, fisting me, slapping me, strap on fucking, and forcing me to lick her pussy. Eventually, I got really good at putting on makeup and I was always ready by 8:00 am.

During all that time, Lucien also came into my room intermittently to request sexual favors. This included throat fucking me deeply and penetrating my ass with his massive cock. Every time he fucked me, precum and piss would leak out of my cock. Chloe would also make out with me, and force me to lick and swallow every bit of Lucien's cum whenever he throat-fucked me. Whenever I leaked out precum and peed while Lucien banged my ass, Chloe would be there to remind me that my cum was worthless, and forced me to lick my own cum and piss.

The couple abused me hard for the next couple of months, and it was then I started noticing changes to my body. The food laced with experimental HRT drugs eventually made me more feminine compared to when I first came to the mansion. One of the most noticeable changes occurred with my chest, as I started to grow out boobs and my nipples started to stick out more. In the first few weeks my boobs became b-cups, and then a few months later they became c-cups. When my boobs grew out, Lucien started to suck on my nipples and smack my tits. Chloe would also punish them sometimes by putting her cigarettes on my nipples, or putting clothespins and needles on them.

Other changes with my body included wider hips, which gave me a more feminine walk. Before I used to be able to walk normally as a man, but now it's harder to balance myself. My hips now move back and forth, and my arms sway more than it used to. My hair which was naturally black, grew out dark brown all the way down to my lower back. My nails grew out longer than usual, and my thighs got a bit fatter from the hormones. I also felt weaker than I used to be, as my arms and legs got skinnier.

Asides from my hands and feet also becoming slender, I noticed my natural 3 inch cock got even smaller. It's now only about an inch long, and very feeble and weak. Before, I used to be able to achieve partial erections, but now my erections are completely ruined by the hormones. On a particular day, Lucien had a doctor come to examine my body, and the doctor declared me to be permanently impotent, meaning I won't be able to have my own kids ever due to a lack of an erection, and very low sperm counts.

The hormones eventually shrunk my balls, and now it's just a bit of loose skin that dangles beneath my impotent cock. Every now and then when Lucien fucks my ass, I can still achieve an orgasm, but only sterile precum comes out. Over time, I also felt a lack of motivation, and became more emotional due to lower testosterone levels and higher estrogen levels in my body. Lucien knows that if he ever left me alone with Chloe, I wouldn't be able to impregnate her, and because I'm much smaller, he knows I wouldn't be able to fight back against Chloe. As a result, he let Chloe abuse me for days on end without his presence when he goes away for his business trips. Those times when I was left alone with Chloe, were truly degrading and humiliating times, and that's a whole different story to tell.