4/5 Sissy Castration Stories – HUMILIATION JOURNEY NEVER ENDS

Here I am once again looking up into the eyes of my tormentor, my superior in every way, especially his cock, 10 1/2 inches to be exact. I know because when I first met him he made me measure it with a ruler. He made me measure mine too. I was embarrassed, humiliated and shamed for being so small.

It hasn’t been called a penis or anything remotely masculine since meeting him. It’s my clitty now and it remains locked in a chastity device. Its usually pink colored but sometimes an unforgiving metal cage with spikes and a urethral insert.

Even though I can’t get an erection while locked up he forces me to take Viagra daily to add to my humiliation. My sex and masturbation days are long behind me now and I balance on the edge of unforgiving arousal and explicit denial of sexual release of any kind.

He stares down at me with a dismissive look, like I don’t exist. All I am is a means to an end, a hole for him deposit his sperm in so he doesn’t have to worry about cleaning up the mess. That’s what I am, his cum hole sissy faggot. It’s my job to give him pleasure. I dread it but know if I protest I’d suffer the consequences. I remain passive in his presence and submit to him completely.

I manage to keep breathing somehow drawing in fresh air around his large black cock buried in my throat. My drool keeps it properly lubricated as it slowly works in and out of my mouth.

I’m wearing pink frilly lingerie complete with garters and silk stockings. The panties are the crotchless kind and my bright pink chastity pokes through the opening. The cage bounces and sways with my bodies motion as my head bobs up and down.

My Double D breast implants are fully healed now and nipple clamps are attached through the peek-a-boo bra I’m wearing. My hair is fully grown out to shoulder length and is colored platinum blonde. That’s how he likes his sissy bitches – big tits and blonde.

My corvette red lipstick is smeared and my eyes involuntarily tear up from the assault of his cock. He orders me to beg for his cum. I’m bound and kneeling, his cock buried in my throat and he wants me to beg for his cum. I try to reason why but I figure he just gets off seeing me suffer the humiliation of trying to speak like this.

I grunt around his cock incoherently for a few moments and it seems to satisfy his sadistic needs. I feel him start to tense up and brace for the inevitable. His grip on my hair is inescapable as he works my head up and down on his shaft.

I’m begging and moaning not because I’m enjoying it but because I know it will get him off quicker and end my struggle to keep from choking or passing out. It works and my reward is the full force of his hands on the back of my head.

His cock is lodged completely in my throat, my nose and chin are pressed against him. I involuntarily spasm from my gut to my throat as the first blast of sperm erupts from his cock. It coats my throat completely. I spasm again and his cum with nowhere else to go is pushed up into my nose. The smell of sperm permeates my senses. He is filling me with his cum and I am powerless to do anything about it.

He’s still hard as he pulls my head off of his big black cock. I work hard to slurp up every drop of his seed knowing that if I don’t I’ll be punished. I manage not to miss a drop, motivated by the thought of not spending the next 24 hours on my knees impaled at both ends by enormous dildos. I’ve learned my lesson.

He unlocks my arms and I’m grateful. I roll onto my side and hear him say that I need to get cleaned up and ready for the party tonight. He walks out leaving me there, limp, locked and feeling like a used cum rag. I manage to pull myself together and clean up the mess.

I begin the rest of my day with a hard workout in the home fitness center. I’ve been given strict orders to keep myself slim. I’ve toned my body down to just 115 pounds and have a nice 23 inch waist. I’ve been working on my hips to get them curvy. Master told me that if the hormones and workouts don’t do the job I’ll be getting some implants to get the ass spanking booty he wants. I don’t want another surgery to recover from so I work hard to get the shape he wants.

I finish my workout and grab a bite to eat and check the computer. I still work to bring in income for my Master. I manage several porn websites as well as provide content for my own. It chronicles my decent into the life of a faggot sissy. My subscriptions are way up since adding the live feed. Of course I never see a dime but what would I spend it on anyway.

When I finish my work I think about getting ready for the party but I feel an extremely strong urge to cum. I know that it’s impossible for me to masturbate while locked up but I have been reading on one of the websites I host about guys who can cum from anal and prostate stimulation. In the past when my Master fucked me I’ve occasionally felt a deep arousal like I might cum but have never ejaculated. All I could ever manage was a puddle of precum dripping from my caged clitty.

I wanted to try to stimulate myself to see if it was possible to actually cum from it so I go to my room and get on the bed with a vibrator. I lube up, insert it, and slowly work it around to find the right spot. I quickly start leaking precum and getting very aroused.

I feel something building deep inside and know I found the right spot. I work the vibe furiously on my prostate and feel my first orgasm since being put in chastity begin to build. Just as I’m reaching the point of no return the door to my bedroom bursts open and I freeze. Its Master…

I cry and beg for forgiveness but it’s no use. He jerks me up off of the bed and pushes me to the ground and drags me like a limp rag doll by the hair. I crawl on my knees trying to keep up. I know he’s taking me to the punishment room.

He orders me to strip and stand, I’m freaking out but manage to do as he says. He slaps my breasts and ass hard enough to leave welts. He bends me over a padded bench and locks my legs and arms to it. My tits are hanging openly as well as my ass and clit cage.

He goes to a nearby table and returns with a large gag with bright red lips and a hole in the middle. I open my mouth to accept it knowing it was best and he locks it in place leaving my jaw stretched wide open. He picks up a riding crop and works my tits and ass until they are covered with more welts. He tells me that since I failed to get ready for the party and tried to pleasure myself he was bringing the party to me tonight.

Before he leaves he inserts an enormous plug in my ass and attaches some wire leads to it and my clit cage. He chuckles as he walks out of the room. About two minutes later I realize what he was laughing at as a jolt from an “e-stim” device is sent from my anus and prostate to the tip of clitty. I take jolt after jolt every few minutes until I’m in a daze.

Thumping bass music brings me back from where I had slipped off to. The lights are dim and I distinctly hear voices, familiar women’s voices but can’t see anyone because its all coming from somewhere behind me. I hear my Master welcoming everyone to the party. I’m still naked and strapped to the bench. My ass and clitty are numb and my jaw aches from the gag.

I feel hands on my head and it’s jerked back and up. Master attaches a chain to the back of my gag and secures it to keep my head and eyes forward. He tells me that he wouldn’t want me to miss any of the party.

I watch as people start to mingle. I catch an occasional stare and laugh from some of them. I realize I know some of the women’s faces, they are my old girlfriends. I’m mortified and ashamed. How could this be happening?

After a while I see a large TV screen on the wall come on. I watch as pictures of me flash across it. Pictures showing my transformation into a feminized sissy. Some of the women gasp no doubt realizing it was me, their old boyfriend who is on display.

They gather around me to examine and it’s Madeline who speaks first. She touches my face and looks into my eyes. She says she always thought I was a little bitch but seeing me this way now her suspicions were confirmed.

She motions to someone and soon a huge muscular black man appears at her side. She whispers in his ear and he winks at her. He steps close to me and unzips his pants. Flopping out is the largest cock I ever seen.

Madeline leans down and whispers in my ear. She tells me she is going to really enjoy watching me suck cock like sissy fucking faggot. She tells me that I need to pay for all the times that I screwed her and never made her orgasm. Madeline tells me that its time for me to provide the pleasure instead of receive it.

When she finishes she steps back and i see the cock in front of me is now rock hard and moving toward my mouth. it pushes in and I can’t stop it. It’s so large that it actually stretches the lip ring gag wider. It slides deeper and deeper until I can’t breathe. I choke and gag but am given no mercy. The cock consumes me and I feel like I’m on the verge of unconsciousness before it pulls out and I can draw in air.

I open my eyes and see my Master standing in front of me. He asks me how it is to see my old girlfriends again. Laughing he goes on telling me most of them have moved on to “bigger and blacker” things. I watch as Lisa my very last girlfriend walks up to him and gives him a long passionate kiss. She thanks him for putting me in my place.

They kiss again and Master looks down at me. He informs me that after tonight my ass is out on the street and that Lisa is moving back in with him. He tells me that I on the other hand have a lot of cocksucking and ass fucking coming my way and there’s not a damn thing I can do about it. I watch them walk away before the cock that was in my mouth earlier returns and my vision is blocked. I am throat and ass fucked all night and in the morning kicked out of the house with a small suitcase filled with street hooker clothes.

With a torn dress and still locked up in my clitty cage I walk away from the house. About a mile down the remote road a limo pulls beside and the window opens up. It’s Madeline in the back with two huge black men. She tells me to get the fuck in the car and get busy sucking on their cocks. I leave my suitcase on the road side and crawl into the limo, I don’t have any other reasonable alternative at the moment.

I suck the two cocks as she tells me that I belong to her now and that I will continue with my work on the websites. She mentions that things are going to get really interesting moving forward and that I have an even bigger set of tits in my near future. I listen and suck until both guys blow their loads down my throat. I remain kneeling and quiet.

The drive is long. I must have fallen asleep on the floor of the limo for a while. Everything that I endured last night caught up with me. I’m startled when one of the big black men slaps my head. Through half closed eyes I look up and see his rock hard cock.

Apparently he is in need of another blowjob from the look on his face. He grabs his shaft and points it toward me. I reluctantly move toward him and open my mouth to suck his huge man meat once again. My mouth is dry and lips are crusted with cum from earlier. As he fucks my mouth the dryness fades to wet sloppy sucking sounds.

As I suck cock I hear Madeline talking on the phone. It sounds like she is making an appointment and my name is mentioned. When she ends the call she gives the limo driver an address. About an hour later we arrive at a remote area with a large red brick building with only a few tinted windows on the first floor.

The limo driver opens the door and Madeline steps out telling me to follow her. I stumble behind her and up the walk way. We reach the entrance and she orders me to strip. I do and stand completely naked except for my pink chastity, I’m scared. A very professional lady dressed in a white doctors coat opens the door. She and Madeline exchange hugs and kisses and go inside the building.

I follow behind them, totally ignored, down a long corridor. A door opens at the and five large black men are standing in a line, naked with their arms crossed.

They look serious. The doctor lady announces that they are the welcoming committee and that I am the guest of honor. She turns and takes Madeline by the hand and walk away leaving me there.

One of the guys points to the floor and I instinctively know what to do. I kneel before him, place my hands behind my back and open my mouth wide. About 45 minutes later I have taken five loads of sperm down my throat.

I’m forced to thank them for letting me suck their cocks then roughly picked up by two of them. I’m carried to a room and strapped down on an examination table. A few minutes later about a dozen people wearing sterile gowns and surgical masks are around me moving medical equipment. One of them starts an IV and injects something into the line. I fade to black.

I wake from a horrible dream and I’m in a panic. I try to move but can’t. My chest feels heavy and theres a numb pain in my groin. I begin to remember where I am and I freak out a bit. The doctor lady is there and in a few minutes I relax and feel stoned. She smiles at me tells me that I was still being medicated to help with my recovery but I would soon feel some new sensations.

She says I was given new breast implants which explained the heaviness in my chest. She also said that I was given a surprise down between my legs and thought I might be happier with the change. My first thought is that they castrated me but I still feel something I can’t explain. She tells me to rest and tomorrow I will be able to get out of bed and begin my adjustment.

The room is dim when I wake up, my restraints are gone and I can move. Gingerly I reach to my breasts and massaged them. They are huge and a lot softer than before. They felt like real breasts, the nipples point out like hard little pebbles. I pinch them slightly and wince, they are really sensitive. I reach to my groin area.

I don’t expect what I feel next… I have a penis, not like my old tiny one. This one is huge. I reach with both of my hands and circle them around it, fuck it’s a real cock, long thick and hard as a rock. My balls are the size of tennis balls and it feels good to massage them. What the fuck has happened to me? Is this some sort of dream?

Cautiously with one hand I fondle my cock and with the other reach up to my breasts. I’m so horny. I close my eyes and start to masturbate. My new cock is so big I struggle to keep it in my grasp. God it feels good. I can’t remember doing anything close to this ever before. After a few minutes I feel an orgasm coming. My cock pulses, my balls contract and I erupt like a fire hose.

Wetness soaks the sheets and my hand is covered with sticky cum. Wave after wave of euphoric pleasure ripples through my body. It is the most powerful orgasm I’ve ever experienced. Strangely though I am still extremely aroused and hard. This has to be a dream.

I think of repeating what I just did but the door to the room opens and Madeline walks in. She says, “I hope you enjoyed that little surprise because it won’t happen very often.” It startles me to hear her and all I can manage to say is “why?”

She explains her plans for my future. I am going to be the star of a new website called Big Cock Shemales in Chastity. She tells me that little cock bitches accept being in chastity easily. However, big titty faggot sluts with large cocks suffer even more humiliation when locked up because they have to potential to actually fuck.

As she talks to me the doctor lady comes in with a needle and syringe. She pulls back the sheets to expose my new huge cock and injects it with something. My penis began to shrink smaller.

She motions to Madeline and says that she has about 5 minutes before it starts to get hard again. Madeline produces a shiny new cock cage from a bag and slides a ring over my cock and balls. It feels tight. She holds up the cage up so I can see it.

It’s engraved with the words “sissy faggot.” She puts it on my now flaccid cock and inserts a barrel lock in place. She removes the key and attaches it to her necklace. I noticed there are at least a dozen more keys attached to it. She tells me that I will be there for another day and then discharged. I will be picked up and brought to her house to get acquainted with my new life.

After they leave the room I feel pain in my cock. It’s trying to grow in its cage but there’s no room for it to expand. I try to think of something distracting but to no avail. I can do nothing but accept the pain and humiliation of having my magnificent new cock locked up.

I get used by the staff repeatedly during my last day here. The men mostly huge and hung black men fuck my throat and ass until I am oozing cum from both ends. The women have me lick their pussies over and over again. It all makes me horny and I want to fuck but that wasn’t possible.

It’s now worse than when I had a tiny dicklette. Now I have a real mans cock but it’s rendered useless. The women tease me and tell me if I ever get loose to come look them up because they would love to have me fuck them with my big shecock. I had no idea what was in store for me next.