How Did I Get to this Point? Ch. 01

Please Cuntress, I said as they were all giggling at my suffering, I can't take it anymore, I need to cum. Please!

How did I get to this point? Horny drunk and in excruciating pain while serving as the evening piece de résistance? It had all started last Monday.

5 days ago...

As I sat down at my computer to check my email, I noticed that I had received 2 messages from Cuntress. My heart racing with anticipation, I opened it, eager to know what mischievous things she wanted me to do this week. It was pretty simple list of instructions but that made me wonder what was coming.

"Worthless slut,

Your tasks for the week are as follow:

#1 -- You are to lock your stupid little clitty up and keep it locked up for the whole week. No cuming for you until you earn it this weekend loser.

#2 -- Daily as soon as you wake up in the morning, you are to sit on your knees for 1 hour while reading the list of erotic stories I will send you that day and stretch your ass. Report when completed.

#3 -- Daily in the evening, you are to sit on your knees for 1 hour while watching the porn videos I will send you that day. While doing that make sure to follow the instructions in the email. Report when completed.

#4 -- You are to only wear panties. Tell me which colour.

#5 -- You are to clean any mess you make the way I have trained you to and send me proof.

#6 -- Friday, you are to come to my place plugged and shaved, for 4:30pm sharp.

Looking forward to putting you to work bitch.

Love, Cuntress"

My cock was so hard reading this but as a good boy, I went to the closet and took out the cage, put it on, then slid up a pair of purple girly panties. Then I opened up the second message.

"My little sissy,

Lube up because it's time to read and build up a nice load... which you can't release you pathetic slut!

Enjoy your blue balls!

Love, Cuntress"

There was a list of 2 stories so I got my butt plug out and started lubing while opening the story. I moved the panties a bit to get the plug in my eager hole. The first one was about cuckolding, where a cuck had to clean up the cum off of his wife as she took multiple cocks in a gangbang. As I read, my cock got engorged and was pushing hard against the cage. Without even realizing it, I was bouncing up and down while my ass was plugged.

I decided to get up, grabbed my dildo and using the suction cup filled my boypussy with it. I then proceeded to the second story, keeping a slow pace riding the dildo. That one was about CBT and had a lot of descriptions. I was close to cuming by the end of it, my balls full and my cock rock solid in the now very uncomfortable cage. I stopped and went to clean up, making sure to put the panties back on when I was done.

I send a message to Cuntress informing her of the colour of my panties and of the completion of the morning task. I then had to go to work which was making me very nervous. Every time I bent to pickup something, I was scared someone would see the panties and ask me about them. As soon as I was done, I booked it home, happy that I had gotten through the first day without issues. As I logged on to the computer, I noticed 1 email was waiting for me.

"Good evening cutie,

I hope your balls are starting to swell and that you are liking the purple panties. Nice and soft on your cage and leaving your ass cheeks nicely exposed are they? Anyway, while you watch the videos, you are to repeat "I am a sissy, I live to serve my Cuntress. I am a bimbo, I do what my Cuntress says". Enjoy the show!

Love, Cuntress"

I got on my knees and started the first one which was a slutty looking girl, gaged with a piece of cloth and tied to a post in her high heels and mini skirt. The camera panned out and a group of 5 men were looking at her in lust, stroking their already hard cocks. They then took turns fucking her holes and rough handling her. Some spat on her and eventually her face was a mess of runny makeup. I kept repeating the statements as I watched: "I am a sissy; I live to serve my Cuntress. I am a bimbo; I do what my Cuntress says". My cock was aching and my balls stung as I wanted release.

The second video was of a girl, tied down on a platform on her hands and knees. There were again multiple men but this time, when they approached her and ripped her leggings it turned out that she was a sissy and had panties an cage just like mine. As they used her, taking turns in her mouth and ass, I was losing my mind with the need to cum. I kept saying the statements, wanting to cum so badly. Eventually the movie was done and when I looked down there was a massive puddle of pre-cum on the floor. As per her instructions, I leaned down and started licking it off the floor, taking a picture of my humiliation. I knew she loved to look at me being a pathetic slut and it made me happy to please her.

After sending the picture along with the confirmation that I had completed my task, I went to bed but it took me a long time before I could sleep. I kept replaying the videos in my mind, imagining that this was what Cuntress had in mind for the weekend and that I would be one of those whores. My cock was very hard at the idea of being used.

Tuesday and Wednesday went without incidents, other than me making even bigger messes. Each time, Cuntress commented my cleanup pictures with some remarks about how much of a loser I was and how pathetic it was to want cum so bad that you'd lick the floor to get it.

On Thursday, I woke up late as I was so horny drunk the night before that it had taken me hours to finally fall asleep. I did the morning routine nonetheless, slipped on a pair of pink panties and tried to sneak in to work 45 minutes behind schedule. As I was finally sitting at my desk, my lateness undetected, I remembered that I had forgotten to send the email to Cuntress. In a panic, I sent one using my work account, trying to explain why it was behind schedule and asking for forgiveness. I spent the day distracted with my balls hurting and fearing the worse for when I got home and opened the evening email.

As soon as I was done for the day, I drove home quickly and opened up my email. Nothing. I had screwed up and now she was probably upset. I paced in the house, checking the email, checking the connection, refreshing the page. Nothing. 45 long minutes later, I got an email from her.

"Good evening sissy,

It looks like today is late day for everyone. I was busy getting fucked by some wonderful stud who had a cock that surely would make a faggot like you drool. Anyway, he pounded me so nicely for hours and I came so much that I lost the sense of time. Tonight I want you to say: "I am a tool for pleasure. My only purpose is to please. I am a sissy slut".

Enjoy the videos, slut, and sure you get up at the right time tomorrow.

Love, Cuntress"

I got into the position and opened the first video. The quality wasn't great and it was a bit dark. I understood why when I saw Cuntress, in a nice set of black lingerie walk into the frame. She dropped to her knees and a man walked up. I couldn't see his face but he had a muscular body and despite his boxers still being on, you could tell that he was hung. She pulled them down and from it sprung a very thick long cock which she quickly got in her mouth. As she was working with her expert mouth, it got fully erected and must have been over 9 inches of glorious beauty. I noticed that Cuntress had been right, I had been drooling while looking at it, and bellow my little cage which was now stuffed, was a puddle of pre-cum.

Cuntress sucked the guy for a while, liking the shaft, worshiping it and the heavy balls attached to it until she was satisfied with her work. They then walked over to the bed where she positioned herself at the edge and guided his enormous member into her wet pussy. He fucked her hard, very hard. You could see her very regularly arch her back and squirt all over the bed but he did not slow down, he did not stop. He kept his pace of relentless fucking. She eventually collapsed and he slipped out.

When she got back up, she turned around and sucked him again, cleaning her juices off of him. She upped her pace and eventually you saw his balls tighten and his shaft pulsate. A big smile grew on her face as she claimed her reward. It was, however, not over for her as he flipped her over and resumed his pounding.

The video was long, about 2 hours and during it the man came twice. By the time it was over, I was a mess: so much pre-cum, my cock hurt, my balls were rock hard and extremely tender and my legs were numb. I pressed play on the next video.

I was a video of a built black man, with a small sissy. He was using her like a fuck doll: moving her about, fucking her ass then her mouth and calling her all sorts of name. I felt like my cock was going to explode through the cage but thankfully it was only a 5-minute video. I really couldn't take much more and I felt like anything could make me cum.

I laid on my side and once the numbness in my legs was gone I licked up the mess and sent the picture I took to Cuntress, confirming the completion of the task for tonight. I surprisingly fell asleep quickly that night, despite being insanely horny with a set of painful balls and nervousness about Friday evening.

I woke up to my alarm, this time at the right time, put on red panties and completed the morning task. The stories were about men using sissies on loan from their mistress which I found very hot. I cleaned up the mess and message Cuntress then went to work.

As a logged into the company computer, I started clearing up emails and notice one of them came from an unknown address with the title reading "Read this ASAP". Likely spam I thought but I checked it nonetheless.

"Hey you fag, u thought u could come in late for work wearing pink girl panties and that no one would notice? Fail! I did notice and now we're going to have some fun. Well... I will but I'm sure u will too. Meet me in the 2nd floor bathroom, the handicap one, at 10:09 sharp otherwise I may have to tell everyone that you're a closeted fag and show them these."

Shaking, I loaded the attachment and it was a few screenshots from the security camera showing me bent down picking up a box with my pink panties showing. I was panicking and the clock said 09:55. What do I do!? If I don't go, whoever this is could leak the pictures and I may get fired because I was late again (I had been late twice already the past year). I didn't have a choice so I got up, with difficulty as my legs where like Jello, and started walking towards the stairs.

Hey, said someone, you look like you're very excited to go somewhere but did you finish the report due today at 11?

I turned around to see my supervisor Jane smiling at me funny.

Not yet, I replied, but I should be good to go.

She smiled again and sat down at her cubicle. I looked at the clock: 10:06. Shit! I started walking fast and up the stairs to the second floor. I booked it through the hall to the bathroom area and entered the handicap one. I looked at my watch: 10:08:38. I was just in time. I noticed there was a bag on the floor so I opened it only to find there was a hood with a mouth hole and a piece of paper in it.

"Take your pants off, sit on the toilet and put this on you fag"

I did as I was instructed and waited. My heart was beating fast and hard: I was so nervous. I however noticed that my cock was hard and pressing against the rim of the cage. I couldn't see anything and all I could hear was my own heavy breathing. Then the door opened and closed. I heard the lock and a chuckle.

Look at this weak ass locked in a cage and wearing panties, said a voice.. They fit you very well given what you are. You're a little fag are you?

It was a deep masculine voice. I wasn't sure what to answer so I just said yes.

That's yes Sir to you fag, replied the stranger.

Yes Sir, I said.

I heard a zipper, then trousers being pushed down and through the hood I could still smell cologne and the musk of a cock.

Open up and work this faggot, he said.

I opened my mouth up and reached forward with my hand until I could feel a very strong leg. Going up on it, I reached the boxers and pull them down. I was then shocked when his cock hit my face. He was definitely packing. I started sucking as best as I could despite the difficulty of fitting him in my mouth and he must have liked it because he was moaning loudly. I was determined to do a good job and the situation was actually turning me on. I could feel the wetness in my panties as my cock was pushing on the cage and leaking profusely from the excitement. I was gagging and my eyes were watering as he started pushing behind my head so that I take more of him in.

Come on fag, he shouted, take daddy's cock. We both know what you like and I'm about to give it to you.

After less than a minute of this abuse and I felt him tense up and I stroke him as hard and fast as I could. I heard a grunt and he started pulsing in my mouth, filling it with warm salty cum. I had to swallow quickly as he was producing quite a lot.

Good, he said out of breath, stay, like a good bitch and wait for me to leave. Then, quickly put your pants back on and go back to work.

I heard him get dressed back up and leave. As soon as the door closed, I removed the hood, put my pants back on and almost ran to my desk. I fixed my clothes by tucking in my shirt and moving my panties and I sat down. There was an email from the same anonymous account.

"Good work fag, I'll be seeing you soon."

Attached was a picture of me sucking his cock. I was not wrong: it was massive and part of me was impressed that I had been able to take so much of it in my mouth. Cuntress had trained me well.

Are you ok buddy? Asked a familiar voice.

I turned around and saw Alexis, my attractive young coworkers, was looking at me with a curious face.

Yes, I said, I'm... ok, why do you ask?

Well, I saw you almost running to your cubicle and well, your shirt was outside your pants which is unusual for you and you...you...

She stopped mid sentence as she looked at me up and down, her eyes going from my face to my crotch. I looked down and realised I had a wet spot where my cage is as I had gotten so excited that it had soaked though once I had put my pants back on. I felt my face becoming red.

I..., I mumbled embarrassed, I must have not shaken enough...

You also have something on your face, she said.

I looked down at the little mirror on my cubicle cabinet and saw I had what was likely dried cum on the side of my lips. I wiped it with my hand quickly.

Oh darn, I said panicked, toothpaste... I just brushed my teeth... I guess I'm having a bad day.

Yeah, right, she said, a bad day.

She winked at me while smiling and sat down. What the hell was that about? I sat down and wondered if she knew something. I looked at the clock: 10:45. Shit, the report. I logged into the application and worked as fast as I could but I only managed to submit it at 11:05. Hopefully no one notices.

The rest of the day was normal, and I left a bit early to go shower and drive to Cuntress. At 4:30 exactly, I pushed the door bell and waited.

She opened the door dressed in a formal looking evening dress and without saying a word signaled me to the bathroom. Once I entered she closed the door and I noticed the clothes on the vanity. I knew what she wanted. I started putting on the pantyhose and the maid outfit, assuming that she would literally put me to work tonight. I changed my panties for the black ones she had provided me and noticed they had a hole at the back. Once done, I exited, got on my knees and waited for her to give me instructions.

I have friends coming over for supper tonight sissy, she said. I will need you to prepare supper, set the table and serve us tonight. I assume you had time to eat something filling at work so I don't expect you to have to eat tonight. As they are my guests, remember that your actions reflect directly upon me and as such I expect you to make me proud. Do you understand?

Yes Cuntress, I said without hesitating.

Get me a drink, she said.

I got up and went directly to the kitchen. I opened the wine bottle and brought her a glass of it before returning to my duties. On the counter, were the ingredients to make a gluten free lasagne, as Cuntress cannot eat gluten but nonetheless very much likes my lasagnas. I was just getting things started when I felt her looking at me. From the corner of my eye, I could see her grin, the wine glass in her left hand and a ridding crop in the other. I soon understood why: I was leaking despite being flaccid.

Overflowing sissy? She said.

Yes Cuntress, I answered.

She laughed and with the crop she slapped my balls. I almost fell to the floor as their sensitivity was beyond belief.

Make sure you don't make a mess all over you pathetic slut, she ordered.

Yes Cuntress, I answered.

After a few lighter slaps, I managed to get the meal assembled, and in the oven. The door bell rang and Cuntress motioned me to the door.

Welcome to my Cuntress' house, I said while opening the door and trying my best not to be seen from outside.

I almost fell down when I notice that standing in front of me was Jane from work.

Well, that suits you much better than a shirt and pants doesn't it sissy, she teased while laughing. I was sure she was pulling my leg when she told me about you but I guess you are really her little play thing are you?

Yes ma'am, I answered.

Ma'am, she replied, I like the sound of that. Now bitch boy, get me a glass of wine and keep it full the whole evening got it?

Yes ma'am, I answered.

I fetched her the requested wine and by the time I was done the bell rang again. Just how many people was Cuntress expecting. I grabbed the handle and opened the door.

Welcome to my Cuntress'..., I said gasping, Alexis... welcome...

Are you going to take my coat sissy? She asked.

Yes, sorry ma'am, I answered shocked by the presence of my next door cubicle neighbor.

Ma'am? she shouted, I'm not 40 years old! You can call me goddess.

She will do no such thing, Cuntress objected from the living room. I am that sissy's goddess but you can be princess since you're young enough to be one.

Fine, fine, Alexis answered. Now bring me some wine boy.

Yes princess, I answered.

As I was pouring the glass of wine, I felt a hand slide under my ass and grab the cage. It was Alexis who had followed me to the kitchen.

Damn you're wet sissy, she said, you like being locked up do you? You like having a bunch of people bossing you around?

Yes princess, I answered.

See, she said, I always found you attractive and I've always liked older guys. I know you looked at me too because everyone in the office want a piece of my barely legal little 18 years old pussy. To be honest I was about to ask you out when your owner, which is a friend of a friend, told me all about your sick little fetish. I must say, I was disappointed at first since I'm sure I would have loved to have felt your hard cock in my tight young cunt.

As she was saying that, my cock was rock hard in the cage, I could feel her hand playing with my sensitive ball sack and my cage, tugging on both gently.

You like that don't you, she teased, you'd love to be unlocked and seed my pussy don't you? You'd love to mount me and breed me?

Yes princess, I answered looking down in shame.

Well, maybe all is not lost for you, she replied getting up on the counter. Here, have an appetizer, slut. Taste what you are missing out on.

I got on my knees and started eating her out. She must have been really turned out because she was drenched. I could hear her moan as I expertly pleasured her sensitive clit.

Damn, she exclaimed, you are fucking good at this!