Sissy's Bizarre Adventure

Hello, everyone! My name is Dray. It has been a few years since I began exploring myself and my sexuality. This story is about how I embraced my desires and became a submissive sissy slut.

Let me start with an introduction. I'm 26 years old, standing at 5'4" in height. I have a chubby physique and a small, tiny 4" dick. Since my teenage years, I have always been drawn to BDSM, submission, and bondage. However, when I entered college, a new fetish for cross-dressing took hold of me. I knew I was different. It wasn't that I was gay or anything, but the desire to dress like a slut and be dominated consumed me.

It all started two years back, I was 24 at that time and I was living with my roommate Alex. He was 25 years old, one year older than me. We were both working guys trying to make a living. I had an office job, and Alex worked as a gym trainer. Alex stood tall at about 5'8" with a muscular body, making him quite the hunk. He would playfully tease me about my man-boobs, often joking that I could compete with any girl. Surprisingly, his remarks brought me a strange sense of happiness. Sometimes, Alex would playfully squeeze my boobs and cuddle with me, blurring the lines of friendship. Although Alex had a girlfriend at the time, I couldn't help but feel that he was attracted to me.

One day, while we were playfully wrestling over the TV remote, Alex pinned me down, and we ended up in a compromising position. Suddenly, he started biting my neck, and with my hands held by his, I was powerless to resist. He continued kissing me, starting with my neck, then my ears, and eventually my lips. It felt like an animalistic desire had taken over him.

I became aroused in that moment, and we engaged in a passionate kiss. He whispered into my ear, "Are you okay?" I replied with a "Yes!"

Alex: I'm sorry if I pushed too hard, but I couldn't stop myself today.

Me: It's fine, Alex. I've been craving this for a long time too.

We both smiled and resumed making out. After some time, I opened up to him about my fetishes. He laughed upon hearing it and asked, "So, you like it dirty, don't you?" I nodded with a smile.

Alex: So, are you gay?

Me: I'm not sure. I want to be dominated and used, whether it's by a man or a woman.

Alex: Okay, so you want to be a sissy bitch?

Me: Yes...! I want it so badly.

Alex: Are you sure about it, bro?

Me: Yes, Alex. You have no idea how badly I want this.

Alex: Alright. Have you ever been fucked or sucked any dick?

Me: No, not yet.

Alex (wicked smile): Then we have a lot of work to do to turn you into a slut.

Me: What?

Alex: Yes, I will train you and make you the biggest cock-sucking slut in this city. But you have to be very serious. You can't go back now. Do you agree?

Me: I am willing to do anything to live like a slutty bitch.

Alex: Okay, it's quite late now. Go back to sleep. We will discuss it tomorrow.

I couldn't sleep the whole night due to the overwhelming excitement. From tomorrow onwards, my life would undergo a complete transformation. I kept imagining myself dressed in all black, with my hands tied, and being used as a cum dumpster by a group of guys. Lost in my thoughts, I found myself rubbing my dick, and before I knew it, I had fallen asleep.

I woke up around 10 am in the morning. Since it was the weekend, I didn't have the office. As I saw Alex drinking his coffee, he greeted me by saying, "Good morning, my cute little slut." I replied, "Good morning, Alex." Suddenly, Alex seemed a bit annoyed and said, "Don't you dare call me by my name. Always refer to me as Master or Sir. Is that understood?" "Yes, Master," I replied. Although I was somewhat shocked, I realized that my handsome hunk was embracing his dominant side right from the beginning. I found myself loving it, thinking to myself how exciting this new dynamic was. Seeing my surprised expression, he calmly asked me to sit down and offered me coffee.

Alex: I spent the whole night thinking about our situation. This new dynamic between us is quite exciting for me, and I do want to explore it.

Me: Okay, Alex... I mean, okay, my Master.

Alex (smiling): As you wish to be a sissy slut, there are a few rules you need to follow.

Me (jokingly): You sound like the guy from '50 Shades of Grey,' making rules for sex and stuff.

Alex: Yes, they are important, both for our enjoyment and your safety. I can't afford anything to happen to my precious slut, can I?

Me: Okay, what are the rules?

 

Alex:

• Rule 1: As you identify yourself as a sissy, you have to stop wearing men's clothes. You will always wear slutty lingerie, pantyhose, thongs, etc., when you're at the apartment. When you go out in public, you will wear panties underneath.
• Rule 2: You will always be ready to suck my dick or any other dick if I wish, and be ready to get fucked in the ass as well.
• Rule 3: You will also serve as the maid in the house, taking care of laundry, dishes, cleaning, and other chores every day.
• Rule 4: Since you're inexperienced, you'll need to practice sucking cocks and being fucked with a dildo and butt plug.
• Rule 5: You need to obey my orders, no matter what.
• Rule 6: You will learn to do makeup and practice applying it inside the apartment. Once you become an expert, I will take you out.
• Rule 7: Once you become proficient in all of these, I will arrange for guys to use you, and your job will be to satisfy their desires.

Do you agree with these rules?

Me: All of this sounds great, Master, but...

Alex: But what?

Me: I want it to be even dirtier. I want to be tortured, tied up, blindfolded, and teased. I want to feel the pain. Also, as a sissy slut, I shouldn't be allowed to feel pleasure. My only purpose should be to please my Master. You should deny me any release, teasing me until the edge but not allowing me to cum.

Alex (laughs): You truly are a slut by nature. Okay, I hear you. You will be tied up and tortured by me and others, but there will be a safe word. If something goes beyond your limits, your safe word will be 'Red,' and if you want to slow things down, the safe word will be 'Yellow.'

Me: Okay, Master, but what about denying me pleasure?

Alex: For that, we can get a chastity device that will keep your slutty cock locked, and I will be the one to decide when it will be opened. From now on, the only way you should experience pleasure is from your ass.

And that's how our journey began, as two guys exploring our deepest desires and pushing the boundaries of pleasure. Little did I know how much my life was about to change, as I embarked on a path of submission, humiliation, and sexual liberation.