Crazy castration fantasy live stream

[slaveboi]

I use to hang out at this local bar a few nights a week. I got to know the female bartender and we became good friends. We usually have dinner a couple times a month and catch up. During the pandemic she lost her job and started an onlyfans to make money. After some time she found sissy humiliation was what worked best for her. I'm not into feminization or sissy play but it was always interesting hearing her stories. When she first got into it I did a few pegging vids with her just to help her get content. She now has a big following.  So a while back I was getting ready for a regular fuck bud on a Saturday.  This girl txt me and asks if I'm busy. I tell her my plans for the night. She asks what it would take for me to come do a live stream custom show for one of her fans. I told her I really wasn't interested as I had a guaranteed breeding that night. She said she would do anything to make this happen and none of her regular guys would do it. I told her if she could find me a guy I would do it but I wanted fucked and a load in me. About 20min later I get a dick pic and I'm like wow that looks good. Well shit. She txt and says probably not your type but this is all I can get at this short of notice.  I ask what I have to do and she comes back with ill get you fucked, dinner, good drinks, and if I'm not happy she will consider doing more. The kicker is I have to wear panties,  do some cbt, and I have to cum while streaming.  So at this point I'm not liking the fem part but I'm liking that cock pic so I give in. She lives 45min away but I'm already good to go so I head out. When I'm about 20min away I get a txt with pic and her saying your breeder has arrived.  So I pull up and she meets me at the door in her dominatrix outfit. We walk into the kitchen and she introduces me to the top less girl that I soon realized is trans and is probably the one with the cock. My friend is running around getting stuff ready and I'm chatting with the trans girl having a few drinks. She finally comes over and says its time to get ready. So this fan sent her a bunch of stuff for a custom video but then asked if she could live stream it that day and offered a ton of money. She has been feminization role playing with him for a long time and he pays her monthly.  So I get undressed and she puts a cock cage on me that was too big and then panties and then she gives me a look and says she sorry but he was very specific and I had to wear a skirt too. I'm sure I looked ridiculous but we walk into the filming room she has. She has me sit in a padded arm chair and uses restraints to keep my wrists down and my ankles spread with my legs over the arms. My friend was all professional setting everything up for the shoot. She pulled up a table with several different sized chastity cages and an elastrator  tool. The last thing she did was squirt some cum lube inside her panties and explained she need to look very turned on. She explained i shouldn't say anything but I should grunt and groan in pain. Everything is set up and the cameras are on i see myself on the screen which is just my lower half. She calls the guy and tells him she is ready.  The trans girl comes in and is sitting off screen with a wicked looking grin. About 5min later the 2nd monitor comes on and I see almost the same view the guy is wearing the same panties, skirt, and has a cock cage. My friend starts the scene telling him what a good sissy he is and its time to make him a permanent sissy. Now I understand where this is going but I'm confused about how she is going to do this for an hour. So she goes on for a bit about how his sissy cock is too big and its time to make it a clit. She tells him he can take his cage off and she takes mine off. I'm not hard cause I'm waiting on the cbt to come. The guy pulls out his cock and starts playing with it. She grabs my balls and starts twisting and squeezing just to the point of being painful. She was getting pretty rough and telling him she was going to have to take his balls too. She zooms in and shows her soaked panties telling him how horny she is and how painful it will be but she wants him to become a sissy for her. The elastrator tool comes out and and she starts pulling my balls through the band and explains to him why she has to get the band all the way to the base so there is nothing left. When the band came off I let out a real surprise yelp. My friend kept playing with my balls and giggling. I was surprised how fast they were turning purple.  Once the were good and dark she said if it was working there shouldn't be any feeling in them. A sharp twist and I groan. I look at the screen and he is stroking his cock and twisting his own balls. She says she better put another band on to be sure. That one hurt a lil less.  Some more playing and dirty talk and I'm swollen and dark purple.  Then she tells him to be extra sure she needs to band each nut separately.  In a few minutes I have each ball banded and 2 on the sack. Its starting to hurt a bit and him thinking we are only 30mim in. She zooms in close and plays with my balls telling him they are already dying and just laughing and giggling. Then she asks him if he wants one more sissy cum before its too late.  He is begging her to please let him cum one last time. My friend whispers to me that she needs me to get hard and cum. Then tells me to look over and see what I get later. I look over and the trans girl has out an amazing cut cock stroking to the show. I'm still soft so my friend starts sucking on me till I'm rock hard. She starts stroking me and I'm looking at my cock with her black nails and I realize this guy has the same color nail polish. I'm just looking back and forth between all 3 cocks getting stroked. I held off as long as I could and right when I started to cum she squeezed my cock super tight so nothing squirted out just a dribbled. She laughed and told him it was worthless and it was time to remove it. Before I knew it she had a band snapped on just under my cock head. She looked at it and said no thats not enough and put another band a little more down the shaft. This continued until she had 6 bands down the shaft. After a little rough playing she looked and said no sissy of hers would have a bigger clit than she does. She stood in front of the camera and pulled her panties aside and pulled out her clit it was surprisingly big. She picked up a ruler off the table and measured it a few ways. Inch and a half! We will make yours a half inch.  By now my cock is purple she stands it up measures a half inch and snaps one last band at the base of my cock. The guy is really jerking it and she is playing with my sad looking cock. She measures to the last band and says oops thats a little short but I'm sure it will be fine. She zoomed in on my cock showing off her handy work. She tells him it will all be dead soon and he will be a real sissy. She said now I'm just gonna tighten these ropes and ill come back in a few hours to cut everything off. That pushed him over the edge and he shot a huge load all over his skirt. She left the cam on for about 20sec and then shut it off. I was freaking out trying to imagine how we were getting all these bands of. My friend came over with what looked like a paint pen and put a drop of liquid on each band. In about 10 seconds they started breaking 1 by 1. When they were all off she wiped my cock down and told the trans girl to help her massage it and get the blood going. Still tied to the chair I was in pain but all the attention felt amazing.  After a few minutes a felt a finger slip down an massage my hole i look down and the trans girl smiles at me and starts sucking my co k and slips a finger in my ass. I got hard fast and she said ok good it works. I get untied and go to the bathroom to look at the damage. I was already black and blue but kinda turned on. I went back out and they were both in the kitchen naked and my friend was cooking dinner. The other girl came over and stroked me back hard. My friend said come over here so I can watch. I bend over the table and she is balls deep in a couple hard shoves.  She paused for a second and said sorry I'm so horny this won't last long.  She starts pounding away and cums in less than 30sec. She pulls out and sits at the table. I'm standing there disappointed and she tells me if you want a second load get over her and show me some respect.  I got on my knees and cleaned her cock and licked her balls and was almost to her ass when dinner was done.  We sat around after dinner and had a few drinks and the trans girl sat back and pushed me down to work her cock again. In short order she was hard again and pushed down on the floor and loaded me in about 10min. She had to leave so I crashed on the couch and drove home the next day with a sore cock but a great memory. Thats only the 2nd trans to ever breed me.