Maddie: Unsuspecting Sissy Whore

This is my first time writing something like this, this is just a crazy fantasy, but maybe I can come close to it in reality sometime! Let me know what you all think, and don't be too harsh 😘 Enjoy!

It had finally happened...I got caught! My wife came home one day while I was taking photos of myself dressed in my hottest sissy attire and getting spit roasted by 2 wall mounted dildos! She asked to see my phone and saw all my correspondence with my online daddy!

I had spoken to her about it before, but always as a fantasy, never a reality! I came clean that I had been secretly sucking cocks occasional daddy cock, sometimes dressed as a sissy slut...I told her how I couldn't keep this side of myself subdued any longer. She left me...I was emotionally devastated, but also felt free to finally explore a side of myself I'd hidden for so long.

Needless to say, the daddy I'd been speaking with knew all my fantasies. I'd told him my desire to dress as a sissy slut and go to the local adult theater and be part of a bukkake with whoever came in. That I wanted to play in the glory hole and get bred by anonymous men. That I fantasized about being gangbanged by other daddies and bbc's. That I wanted to be the main attraction party for large parties and get used and filled with cum. That I secretly wanted to be a sissy prostitute, that sucked dirty old men off and got fucked for money in order to pay for all my sissy clothes and sissy lifestyle. With my new freedom we set up a time to meet...and with all the excitement I'd forgotten all the crazy stuff I'd divulged to him.

I was so excited! I finally was able to shave my body totally smooth, shave my legs, do my makeup...live full time as a sexy sissy! The first few times I met my daddy were relatively tame. Normal play with some wild additions, but nothing crazy. But we kept evolving! He picked me up one day and I was under the impression we were going to his house. He told me, walk out to my car in your sexiest sissy outfit! I'd never been out in public to this point, but desperately wanted to please my daddy! So I did! I was so scared, trembling as I walked out the door in a short black party dress, black heels, thigh highs and a sexy red wig! But I made it!

Daddy started to drive and asked that I suck his cock! I happily went down on him, not paying attention to where we were going! I slowly started to suck his half hard cock, licking it up and down, playing with his head, pursing my lips together and running them up and down his beautiful shaft. Then I started sucking him deeper and longer, with lots of thoughtful strokes and lots of spit, making his cock so sloppy and wet! Then I started deepthroating him occasionally and teasing him a bit, trying to edge a bigger load out of him. Finally I felt him starting to tense and cum! He held my head down and shot directly into my throat! It was such a big load!! I was able to handle most of it, but I choked a bit and some cum shot out of my nose! I was a little embarrassed but also really turned on!

While I gathered myself and cleaned up, I didn't notice we had pulled in to the local adult store! I said omg daddy, I'm so scared, I don't think I can! He said "Maddie, I've secretly been video taping all of our sessions, and I've seen who you are for real. If you don't go in there and do exactly as I say, I'll tell everyone! I'll release all the videos!" I was so scared, and nervous, but what choice did I have? I mean it was one of my biggest fantasies! It didn't take a lot of convincing because I was so hot from sucking daddy's cock. So I went in...

It was Saturday evening, it was busy! Lots of people around, women, other crossdressers, older men, younger men. Daddy made sure to walk me around a little then directs me to a room where they're playing porn, it had a little stage up front. There may have been 10 to 12 people In the room. Some were playing, most were watching the movie. He made sure to walk me up to the front then told me to sit. He took his cock out again and told me to suck it again, and get it ready to fuck me. He whispered in my ear "I'm going to bend you over this chair and fuck your pussy so all these people can see what a slut you are! You're going to suck/lick any cock or pussy that comes in front of you, and you're going to let any takers fuck your tight little pussy!" He reaches down and starts to feel my tight hole. "I'm glad you decided to lube yourself up" he said to me.

I was so nervous! I'd only ever been with a few men, and played with my dildo. I wasn't sure I'd Be able to handle what was about to happen, but what choice did I have!? I was also nervous I wouldn't have any takers, but that fear would soon change. Daddy was now fully hard and he pulled me up and bent me over! I made sure to arch my back like a good slut. His nice 8" cock started pushing its way into my sissy pussy. It felt so amazing, I felt my eyes roll back into my head a little and felt my locked cock start to tingle. Then I felt daddy wrap a condom around my cage and muttered to me "any cum you shoot you'll eat later". He started fucking me more and more vigorously, like he never had before! I was enjoying the hard fucking in front of all these strangers. Some men started asking daddy if they could play with me, he happily informed them when he's done, she's all yours! I had lines forming in front for my mouth and behind daddy for my pussy! Daddy started really fucking me hard and I knew he was close. I was so hot, I wanted to impress him, so before he came I yelled out to the room "daddy wants me to let all of you all use me for as long as you want, and cum wherever you please. Please fill me with all of your cum! Breed me, feed me, make me your cum dumpster today! And tell the store there's a sissy for use all day! Post it on any app too! I'm here to be fucked and filled!" As I yelled that daddy Moaned with pleasure and pumped my pussy full of cum!

It seemed like no time passed from when he filled me up that I had a new cock in my ass and I had two cocks in my face! I was in heaven! I started sucking and stroking the cocks in front of me! I had never let go like this before but I was loving every second!

Before I knew it one of the cocks I was sucking was exploding in my mouth. The other seemed to be shooting endless ropes of the thickest cum I've ever felt onto my face. Quickly 2 more cocks appeared and I wasted no time getting down to business. I was in the zone, I was a cock sucking machine, giving the sloppiest most loving blow jobs. "I was made for this" I thought in my head. As I was thinking that I felt ropes of cum getting blasted into my pussy. I couldn't believe I had let a total stranger fill me with cum...but then I remembered I didn't really have a choice! And that made me so hot!

I noticed the next cock starting to probe my leaking pussy...and holy shit was it big! I turned around and saw a beautiful black man with amazing thick thighs, nice pecs and hard abs. He was so sexy! I turned and asked him if he was going to cum in my tight sissy pussy? He responded "when I'm done with you you'll never want another cock than mine. And If your good, I might make you mine!" I didn't really think about it, but I just yelled "make me your sissy bitch please!" And I grabbed his delicious ass and pulled him into me. I gasped as I never had something so big in my ass before. But it was bliss! He worked his cock deep in to me with patience and started pumping with more and more meaning! I was so lost in his cock I barely noticed the 7 additional loads I had swallowed. I had never felt such pleasure!

I started noticing my caged cock swaying to the rhythm of his pumps. It felt so good, and with a few more pumps I was overtaken with bliss, my clitty started leaking uncontrollably into the condom hanging from my cage and my legs started shaking and I realized he was now filling me with his cum. I felt his cock soften as he slipped out of my cum filled pussy. I was in love with his cock...but there was no time to bask in my pleasure! The cocks kept coming, literally! I was dripping with cum from my face and his cock was immediately replaced with another! I noticed a line out the door for both my mouth and my pussy! And I noticed it wasn't just men, it was women, shemales, you name it! I was in for a long night! I wasn't sure how I was going to make it, I was already getting full from cum, and I noticed the sizable pool of cum that had dropped from my pussy...but I had to do exactly as daddy said!

The pleasure continued for hours and I loved every minute of it! But I noticed the end of the line, and I thought to myself I can finish this, even though I didn't want it to end! When the last few cocks we're waiting to get serviced I noticed daddy was nowhere to be found. And it was then the theater owner joined the line for my mouth. He was going to be the last one! Once I got through the 5 cocks before him, he had already been edging, his cock was out! I immediately started sucking with the same enthusiasm I had the whole time! He told me "I've never seen anything like this here! I counted, 77 people came in this door! And I'm pretty sure they all got in line for you! And you're daddy, he came up to me after about an hour and said that he didn't know it'd go this far and that he was sorry he couldn't be your daddy anymore. But he told me a gentleman, I think that first big black cock you handled Offered him $500 for you, and he took the deal." It was at that point I briefly stopped sucking his cock, and replied "huh, he sold me?" Then the gentleman named Jerry came into the room and said, "don't you dare stop sucking that cock, your deal with your last daddy still applies with me!" I immediately resumed my duties! Jerry continued, "but we have a slight change in plans..." he smirked as he took his hard cock out "while I fuck you I'm going to explain your new life. He pushed inside my dripping pussy again...he felt just as good the first time.

"Remember when you said make me your sissy bitch?" I barely did, but I recalled as I kept sucking the owners cock! "Well after, I thought about how good you were at taking my cock, and how much of a show you were putting on and thought I could make some good use out of you! I went and had some of my buddies grab some cameras and shot the hole thing! We're going to produce it and sell it! After me, you fucked and sucked 75 people, maybe more than once! I'm gonna name it, 'Unsuspecting Sissy Whore Takes 77'. And since you're life will be over after that, you're going to be my personal sissy whore! I'm going to fuck you when ever I want, I'm going to let my friends fuck you whenever they want, and I'm gonna send you out on the streets when your not cooking or cleaning for me or fucking me or my friends! You're cock will stay locked up! And you will be my sissy bitch!" It was at that moment I realized how much cum was in the condom attached to my cage...and still couldn't comprehend what was happening to me. But I didn't stop sucking or bouncing on Jerry's amazing dick!

He continued, " does any of that not make sense you sissy bitch? Don't stop sucking when you answer!" I replied with a full mouth "no daddy! I am your sissy cum whore and you can use me anyway you'd like!" It was at that point the store owner pulled out and shot another load onto my face that was full of dried cum and he slipped off into the distance!

I moaned with pleasure at what I slut I had become today as I felt Jerry's cock start to pulse! I knew he was close, he started to pump harder and deep with all 10" of thick meat! I came again filling my condom up more! He said "here's one more load for your sissy ass!" He thrusted and pumped and stayed in me while he filled me again!

I was exhausted, but satisfied! He slid out of me again and I knelt in exhaustion. I had no idea what time it was, but I knew what a good sissy slut I was. Jerry demanded that I eat all my sissy cum, and I quickly obliged, then he added "and lick up all that cum on the floor!" I looked down and saw all the loads that had poured out of me...I bent over and happily licked it all up! I had never been so satisfied! I looked at myself, I was covered in dried cum, as were my clothes. My heels were sticky with dried cum, my thigh highs ripped and torn...I pulled my phone out and took a selfie. My wig was ruined and my makeup was smeared but I was sexy!

Jerry called to me "come on sissy, let's go!" I happily followed him out with what strength I had left and jumped into his car thinking about what new surprises my new life had in store!

More to cum!