3 Day Weekend - Day 03

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Sissy faces new challenges and finds her place.
3.6k words
4.49
8.8k
7

Part 3 of the 3 part series

Updated 06/10/2023
Created 06/16/2021
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Sjen451
Sjen451
188 Followers

I step off the bus in front of the hotel. In the window I catch my reflection and notice the pink cock cage is visible through my thin little sun dress.

I'm wearing full makeup and heels. Nothing under the dress, and a wide leather collar around my neck. A few toys in my backpack.

I proudly walk through the front lobby holding my leash in my hand. I take the elevator up and walk down the hall to my daddy's room and knock on his door.

He greets me with a smile as he opens the door to find me dressed appropriately this time.

He compliments me with, "You look very lovely today my little slut. How was the commute?"

"It was exciting!" I exclaimed. "I could feel so many eyes on me, it made me feel like the center of the world. I can't believe I've never done that before."

"Well I'm glad you are enjoying being yourself in public finally. I assume you made it home alright last night?" He asked.

"Oh yessir." I responded. "With the help of some very nice gentlemen. They took turns using me in their van, then another man brought me home. I think he wants me to be his personal slut. He put me in chastity and took my keys."

As I said it I realized I may have made a mistake so I quickly cried, "OMG! I'm so sorry daddy. I should have asked you first if that's ok. B-but I didn't have a choice, he just took control and I didn't know what was going on until-"

Daddy interrupted my apology to say, "it's ok to have more than one daddy. It means you are an overachiever, and I'm proud of you for giving yourself to more men."

A rush of relief flowed through me.

"And that brings me to tonight's agenda," he continued. "You have the eagerness and potential to please so many men by being anything they want you to be. Your talent and drive for pleasing your superiors is already impressive, but tonight I want to expand your capabilities."

"Yessir," I responded. "I will do anything you ask of me."

With a smile, he says,"I know you will. But tonight you won't be doing anything for me. Three men have arranged to arrive tonight so you may help them experience their sexual fantasies. They don't just want a young little slutty boi to play with. They each have a specific fetish, and I think it's time you learned how to adapt yourself to meet different needs."

"That sounds exciting sir. What do they want me to do?" I asked.

"No, no," Daddy corrected. "I'm not going to tell you. It will be your job to get them comfortable enough to tell you what they want."

And with that, there was a knock at the door.

"Ah, the first gentleman. Remove your dress and sit on the bed." He instructed.

I did as I was told. Legs crossed, hands on my knee, sitting on the edge of the bed wearing heals, cage and collar.

I heard some muffled talk at the door before daddy reentered with a tall gentleman beside him, wearing what looked to be a lab coat.

The tall man looked me over then reached in his pocket and handed daddy some cash.

I smiled at my new friend and patted the bed beside me as I said, "Won't you please come sit by me mister?"

He returned my smile as he walked over to me and sat down.

He reached out and gently caressed my smooth thigh as I leaned in and gave him a little kiss before whispering in his ear, "My daddy tells me you have something very specific in mind. I want you to know you can do anything you want. Don't worry, I won't say no."

To that he responds, "Well actually, that is kind of what I am looking for. Someone who won't say no. Or anything for that matter."

As he continued he slid his hand deep into my crotch then pressed the tip of his middle finger into my wet, lubricated hole.

I let out a slight moan as I gently nibbled his ear.

"I work around coma patients all day," he continued. "And sometimes I see an attractive girl and I just want to have my way with her when I'm alone in their room. But I know that's wrong, and I would be fired. But the urge is still there.

I'm told you are very good at lying still. So what I want is for you to lay unmoving on your back, and let me do all the things I could never do in real life. I want to touch you, and kiss you, and penetrate you, knowing you will not react and will never be able to tell anyone. Will you be my secret patient?"

"Yessir," I replied. And with that instruction I lie back on the bed with my arms at my side and my eyes closed. I try to let all my muscles go limp.

"That's good" he says, "but I need you to keep your eyes open. Looking towards the ceiling, but at nothing at all. I need you to have a blank expression."

Silently I obeyed, staring blankly toward the ceiling.

First he simply watched me for a while. Maybe to get the sense I was like his patients at work. But eventually I felt his fingers slide slowly across my chest and nipples. He then pinched my nipples and sucked at them. He ran his tongue from my naval to my neck. As he kissed me on the lips I didn't move, I didn't even blink.

He took my limp arm and stretched it out to have my fingers run down his lab coat until he held my hand at his exposed erect penis. He softly curled my fingers around his shaft and jerked himself slowly with my hand. He moaned, but stopped before he climaxed. He set my arm back in place beside me. Then I heard the familiar sound of a latex glove going on a hand, followed by the sound of a lube pump.

While still lying on my back, he stood at the end of the bed and parted my legs only slightly before I felt his cool, slimy fingers move towards my sissy hole. I felt his hand against the inside of both my thighs as he began easing his four fingers inside me. Rather than moving in and out, he only twisted his hand left and right as he continued to push into me. My breathing quickened as the largest part of his hand and thumb entered my hole, but I managed to keep my breathing silent.

This seemed good enough for him. After a momentary pause he pushed the rest of the way in, and it felt relieving as my sphincter closed around his wrist. His hand continued to twist and move inside me as he licked and kissed my thigh.

Then he raised my leg and crossed it over the other one, holding them tight together with his free hand as he very slowly pulled his other hand from me. My hole expanded then closed as he pulled himself out of me.

Then I heard him jerking his cock until a splash shot across my belly.

I remained motionless as he pulled up his pants, removed the glove, leaned over and kissed my cheek. As he did this he whispered a soft thank you.

I moved my eyes to catch him smiling as he turned to leave the room.

As daddy escorted him to the hall I reached down with my finger to wipe up the semen on my stomach and greedily sucked it off my fingers.

Before daddy even closed the door he began praising me. "Well done, my dirty little girl. I wasn't sure how you would do with that one, but you were magnificent!"

"Thank you daddy. I kind of enjoyed that too." I replied.

"We haven't much time until the next one arrives, so I should give you a little advice before he gets here. As you already know, a little role playing goes a long way with most men. But some want something more unreal. Sometimes you need to take on an entirely different sort of role to give a man just what he needs. So I advise you greet him on all fours, and try not to talk too much." Daddy instructed.

As the man entered, he looked down at me sheepishly. I couldn't tell if he was excited or nervous. But again I saw daddy take money and stepped out of the room.

Looking up at him I introduced myself. "Hello sir. I'm your slut this evening. What would you like me to do for you?"

"Ah, well that's refreshing to hear." He said. "I like when a slut knows her place. But tonight I don't want a slut, I want to be loved by a real bitch. You're already wearing the collar and leash. Now bark if you understand what I'm telling you bitch."

"Bark! Bark!" I replied.

"Good. That's good." He said with a sense of satisfaction.

With his encouragement I got into character. On all fours I started prancing around the room and barking. I saw him smile as he watched me run around.

"Come here girl!" He commanded. I ran over to him and when he told me to sit I sat back on my rear legs and panted heavily for him. Holding my leash with one hand he reached down and pat my head. As he did I tilted my head up and licked at his fingers.

"Oh I see you're a hungry little girl. Well I think I've got just what you need." With that he reached into his bag and pulled out a jar of creamy peanut butter.

I smiled, and barked in excited anticipation. He dropped his pants, and when he did I ran around behind him and buried my nose between his buttcheeks while making overly exaggerated sniffing sounds.

He laughed as he was dipping his balls in the jar, being sure to cover his genitals well.

"Sit girl!" He commanded as he tugged at my leash. I obey and he turnsto face me. I see the brown smothered scrotum and really begin to salivate.

"Lick it up girl. Lick it all off." He commands.

I happily sit before him, with all fours on the ground hungrily lapping at the hanging treat. I get peanut butter all over my nose and face as I lick his balls clean. But eventually the peanut butter becomes too much and I can't swallow it. I just spread it around with my tongue as his hard cock bounces off my forehead.

He reaches behind me and grabs my ass while commenting, "I feel a lot of heat coming off you. You really are in heat aren't ya bitch?"

I look up at him and wimper.

"Well don't worry, I know just what a bitch like you needs."

He reaches his fingers into the jar of peanut butter and scoops out a handful. The he reaches behind me and I feel his fingers pushing it into my hole.

"Your gonna really like peanut butter when I'm done with you. Now pu your ass in the air for me".

I do as he tells me and he kneels down behind me. It feels so dirty as his cock slides into me through the creamy peanut butter. I wimper for him as he begins fucking me doggy style. He holds my leash tight as he fucks my bitch ass. The additional friction really feels great and I begin to howl as he shoots his load into my messy ass.

Before he's even finished cumming he says, "Suck me clean bitch. Now!"

Yanking my head around to him with a sharp pull of my leash. Immediately I wrap my mouth around his cock, catching his last bit of cum, combined with the flavor of my own ass and peanut butter.

He holds my head down on his cock as he repeats "Suck it bitch! Suck it you dirty bitch!"

I find myself really enjoying being his bitch as he berates me the entire time I'm licking and sucking him clean.

He ensures his entire pelvic area is completely clean before he releases my head.

He stands up and puts his pants back on. Before leaving he bends down and kisses me on the mouth, pats my head and says, "good girl."

Daddy talks to him in the hall for a bit as I go to the bathroom and clean myself up.

I'm still in the bathroom when our final guest arrives. He walks in on me in the bathroom and I apologize, "I'm sorry, I'm just cleaning up. I'll be right out."

He says, "No bitch. You're right where you need to be."

I'm a bit alarmed and incredibly turned on. If a big ebony alpha like this wants me in the bathroom, then I am happy to remain in the bathroom.

"Where's your toys bitch? I need to see what you got." He commands.

"I-in the bag. O-on the c-counter," I respond.

He empties my bag, finding my favorite big black dildo, but plug, and horsetail whip.

"You like black dicks?" He asks as he's looking at my dildo.

"Yessir, I love black dicks.." I respond meekly.

"Do you like getting filled?" He asks.

"Yessir, I love getting filled." I respond.

"I'm gonna fill your little ass up. I'm gonna make you bulge and explode. Do you want me to make you explode?" He asks.

"Yessir." I respond. Not really sure what he means, but sure I want whatever he's got.

He commands, "Turn away from me. Face the toilet, and bend over with you elbows resting on the back of it."

I do what he says. Bending over at the waist, with my legs on either side of the bowl, I rest my elbows on the back of the toilet.

I hear him undress behind me. I turn my head to see his naked body. My clitty leaks at the sight of him.

I feel him spread my cheeks with his hands and he inserts just the tip of his penis in my ass. I try to back up onto it but he smacks my ass and tells me to hold still.

A few seconds after resting the tip of his cock in me I feel him release and flood my asshole with his hot piss. As he continues I feel his warm urine climbing deeper into my colon. After a minute he is still shooting a strong stream inside me as my belly expands to take it all. It's hurting deep inside my guts before he finally run out.

He orders me to clench tight as he pulls his head out. I feel something press against my back door again.

"I'm gonna shove this buttplug in your ass so you don't spill any of my golden gift. Don't spill a drop. Do you understand?" He asks.

"Yessir, I understand." I reply as he presses the large plug into my already-full hole. I am careful to clench the base of the plug tight as it enters me.

With my stomach bulging from his Golden enema, he hands me a bottle of water as he takes one for himself.

"Now chug!" He commands. "This was just the start."

We both finish our waters and he gets us both another one. After he makes me finish three, and he has five he has me walk out of the bathroom where daddy is waiting in his chair, no pants on, soft cock ready to go.

"Go suck his dick." The man orders.

I crawl to daddy on my hands and knees, moving carefully so I don't spill.

As I place my mouth on daddy's sweet cock I feel the sharp sting of the whip as the man lashes my exposed ass.

Luckily I had enough control not to bite down.

Daddy gently grasps my head and says, "Good. Now get ready to drink."

With his dick still in my mouth he begins to sputter his urine out. He doesn't have nearly as much as the man did, but daddy still finds a way to test me. As I start chugging he holds my nose, preventing me from breathing until it's all swallowed. And to make it more challenging, the man is whipping me hard.

Finally I finish the last of my daddy's drink and gasp some air with my mouth opened around his now erect cock.

If daddy would allow it I would be screaming in pain with each belt of the whip. (Even though daddy doesn't approve, I'm a really good screamer and I know a few guys who really enjoy making me hit the high notes). But I know I can't do that, so I keep muffled by sucking his dick as the man keeps whipping me.

I can feel my butt want to release the plug, but I can't let that happen. I have to keep the pee inside me.

But with all these distractions I am unable to give daddy a decent blowjob and it takes him quite a while to cum. When he finally does he holds his cock down my throat with my nose plugged, as he likes to do.

By this time my own bladder is feeling full and I need to pee, in addition to my belly already being bulged from my enema.

I really can't hold it much more.

That's when the man orders me back in the bathroom.

He has my big dildo suctioned to the rear of the bathtub wall.

"Carefully remove the plug, crawl in the bathtub on your hands and knees, and back your sissy ass up onto that dildo. And don't spill a fucking drop." He warns.

I do my best to obey. Gently removing the plug without allowing any liquid to escape. Then, in the bathtub I backup onto the dildo, again being careful not to spill. But it's much harder to keep a tight seal on the dildo. And to make things worse, he grabs my shoulders and pushes me back on it even deeper.

Now he kneels in front of me and sets the head of his ten inch dick in my mouth. He lets loose with another torrent of pee.

"Swallow it you fucking slut! Swallow it all" he yells.

Just as he finishes, and my stomach feels like it's about to burst, he rams that massive cock deep down my throat. As he skull fucks me my body can't take it anymore. He triggers my gag reflex and all the urine in my belly comes up in a massive tidal wave. Right when this happens he pushes me back all the way in the dildo, and my sphincter just can't hold it back anymore and my enema shoots out around the girth of the dildo.

As my ass and mouth release waves of urine I can't control my bladder either and my little caged clitty starts pissing like a horse.

As piss is shooting out of all my holes the man pulls his enormous cock from my mouth and pulls me forward, off the dildo.

I felt a rush of relief stronger than any orgasm as my body violently purged itself and my mind was blanketed in euphoria.

When I finally regained my senses, I was a wet mess curled in the fetal position in the bathtub. I couldn't move. I didn't want to move. I just laid there like a deflated balloon until eventually daddy came and turned on the shower to a nice warm temperature for me.

I laid there a while longer, now feeling like a clean empty balloon. Left with a deep craving to be filled again and again.

"Are you still alive?" I hear daddy ask from the other room.

"Yessir. I'll be out soon." I say as I carefully ease myself up and find a towel.

"Your street clothes is in the bag in the corner in case you want to get changed before heading home." Daddy says.

I look around and see the bag he is referring to. It seems the man with the gorgeous cock had already left.

"No thanks," I say. " I don't need it. I would rather wear the sun dress".

"I think it suits you better." He agrees.

"Here's your half of the money you earned tonight. You really have a knack for pleasing men." He says as he hands me $300.

"Thanks.. I guess I do.

Say, do you think maybe I could do this all the time, like as a job?" I asked.

"I don't see why not. Is that something you would like to do?" He asked.

"Yeah, I think it is. Well, I would still be willing to help people for free, but its what I'm good at. And I don't have to pretend to be something I'm not while I'm doing it. I'm a sissy. A good sissy" I said.

"Yes you are. Have a good night, we can talk more later". Daddy said.

As I took the bus home, enjoying the eyes on me, I thought more about it and my career decision just seemed right.

And when I got home to find my new daddy had went ahead and installed cameras in every room, that cemented it. I will be a pay-to-play web sissy, willing to do whatever men need on camera, allowing 24hr access to me at all times. And with my other daddy helping line up live hookups, there will always be something fun going on to watch at my house.

Thanks for spending the weekend with me you guys. *kisses*

Sjen451
Sjen451
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AnonymousAnonymousabout 2 months ago

I liked it, but thought the first part was the best of it all.

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