New Story “Sissy Milking” Chastity and more with my faggot Sissy Cassie!
Sissy Milking
“Faggot, get over here.” yelled Mistress Andrea. Sissy Cassie hurried into the room and immediately knelt before Mistress Andrea. “I am worried Faggot that with the way I have taught you to crave cock and swallow cum that you will be tempted to miss-behave and touch your sissy clitty and cum without My permission.” “Sissy will not.” Cassie started to say, but Mistress Andrea slapped him hard across the face and sternly said, ” I didn’t tell you to speak Faggot, so shut up and don’t interrupt Me again.” Sissy Cassie bowed his head as Mistress Andrea continued, “because I don’t feel that I can trust a whore like you, I have bought a new chastity device to encase that sissy clit of yours in, and it will be locked in it 24/7. No matter how much you are tempted faggot, no matter how much I make you want to cum, the devise will not permit that clit to do anything. Seeing your anxiety over this will please Me greatly.
I love to torture you, humiliate you, and make you know that you are nothing but a piece of My property, that I can do anything I dam well please with. You are a fucking faggot, and deserve no better treatment. Now stand up Faggot and lift the front of your dress.” Sissy Cassie did as he was told, and Mistress Andrea roughly pulled his panties down. Mistress took the ring of the chastity device, and fit around Sissy’s balls and clitty, then slid the cover over his clitty, pushed the ring and cover together, slid in the locking pin and secured the pin in place with a lock. “Perfect!” exclaimed Mistress Andrea as She pulled on the chastity device to make sure that it fit tight, and would not come off. “Maybe, and I mean maybe Faggot, I’ll put you on a milking schedule of some sorts, but completely denying you of any release, is very appealing to Me.”
Sissy Cassie stood before Mistress Andrea with a look of total despair, but knew better than to say anything. As he did Mistress Andrea said, “I’m sure Faggot that you are thinking that one positive thing about having that clitty encased is, that I will not be able to beat it with My crop. Well that may be, but let Me show you that your fucking balls are still exposed to Me.” As Mistress Andrea said that She pulled the shaft covering of the chastity device up, and back and slapped Sissy Cassie’s balls hard and fast three times. Sissy Cassie screamed and the pain made him bend forward. Mistress Andrea stood there laughing, and said, “this is an opportunity too good to pass up, stay in that position Faggot.” Mistress Andrea walked out of the room leaving Sissy Cassie still writhing in pain. When She returned Mistress began to paddle Sissy’s ass repeatedly until it was crimson red and his eyes were tearing. Once satisfied Mistress said, “pull up your panties and fix your dress, and get about your chores Faggot.” Sissy Cassie quickly did as he was told and hurried off to clean the bathrooms.
As each day passed, Mistress Andrea took great pleasure in teasing and tormenting Sissy Cassie about his chastity. Mistress even took Sissy to the adult bookstore to buy some fag magazines and movies, something She never permitted Sissy to have before, this to further torment him. The first time Mistress allowed Sissy to watch a fag movie She waited until She could sense the growing desire in Sissy for release, and said, “do you want Me to let you stroke Faggot?” “Yes please Mistress, please,” pleaded Sissy Cassie. “You do, don’t you Faggot, you want to feel your little clitty in your hand, it has been so long hasn’t it?”
“Yes Mistress Andrea it has been, please let Sissy touch it.” Sissy Cassie pleaded again. “Go ahead Sissy and stroke,” replied Mistress Andrea. “But Sissy’s clitty is still in the device Mistress,” whimpered Sissy Cassie. “I know, but stroke the shaft cover and see if your clitty will grow,” said Mistress. Sissy began to stroke the shaft cover, the desperation in him mounting as his excitement grew from watching the men suck and fuck each other. “How does that feel Faggot, is your clitty growing in its cage?” asked Mistress Andrea. “Sissy can’t feel anything Mistress and its clitty can’t grow in this. Please take it off Mistress, please let Sissy touch himself it has been so long and Sissy has tried to be good,” cried Sissy Cassie. “Yes it has been a long time and you have been behaving yourself, but no the device has to stay on. You need to learn control, and frankly your agony is amusing Me to no end. Keep watching the movie and keep stroking the shaft covering until it is over, and you long to be the fuck toy of those fags in the movie.” Mistress left the room and Sissy stood dejectedly stroking as he longed for release. Situations like that played out most days and Sissy began to resign himself to the fact that Mistress Andrea was likely to never allow him to cum again.
Almost two months of this torment had gone by and Mistress had never brought up the possibility of Sissy’s release from his device. As time when by in their relationship, She had come to take more and more pleasure in his pain and debasement. Once Sissy had finished cleaning Her breakfast dishes, Mistress told him to go to the training room and take off his dress and panties. When Mistress Andrea entered the room She cuffed Sissy’s wrists and hooked them above his head to a short length chain the other end of which was attached to an eyelet in the ceiling beam. Mistress Andrea did not say a word, She simply walked over to the wall where Her whips hung, selected a single tail and began to whip Sissy’s ass, bringing screams from him and causing welts to almost immediately appear. When She was done Mistress Andrea grabbed Sissy’s face and said, “that was just to make sure You know that I own you and can do whatever I want to you.” Sissy just nodded acceptance as the tears streamed down his face. To Sissy’s surprise Mistress Andrea then unlocked his chastity device and removed it. Before doing anything else She shoved a vibrator up Sissy’s ass pussy and turned it on. Mistress then said, “I am going to milk you Faggot, but realize that the device is going back on right after that and it may or may not come off again.” “Sissy understands Mistress,” replied Cassie excitedly. Mistress began to stroke Sissy’s clitty while moving the vibrator in his ass pussy.
As Sissy began to become aroused Mistress told him that he better not cum until She told him to. “Do you want to cum Faggot?” asked Mistress Andrea. “Yes Mistress please,” replied Sissy Cassie. “Not yet Faggot,” said Mistress as she turned the vibrator fully on. “Please Mistress Andrea, please let Sissy cum, please Mistress please.” “Faggot wants to cum?” asked Mistress in a teasing voice. “Oh please, Mistress let Your Faggot cum, please.” Mistress Andrea picked up a shot glass and said, “cum now Faggot and squirt all of that juice in this glass, if you miss putting a drop in I am going to beat you.”
Having not cum in so long Sissy came hard as Mistress guided him to the glass. “Drink up Faggot,” ordered Mistress Andrea, and Sissy hungrily swallowed his cum and then licked the glass clean. “Thank you Mistress Andrea for allowing Sissy the privilege of cumming and also allowing him to eat it,” said Sissy Cassie. “I am going to take your cuffs off, when I have I want you to lick up any oozing from your clitty and then go wash it. Be quick about doing so and get back in here so I can re-attach your chastity device, then I want to discipline you some more,” instructed Mistress Andrea. Sissy licked up the cum drippings, hurried off and then returned to Mistress. She re-attached his chastity device and locked it in place, then bound him to the cross and began to whip, paddle and cane him. Sissy’s screams and pain aroused Mistress Andrea and She took him from the cross and made him pleasure Her.
From then on Mistress Andrea continued to take great pleasure in denying Sissy his release and in making him wait for long periods to be milked. Sissy’s anxiety from longing to touch himself and cum was constant, but he knew that he was Mistress Andrea’s possession and She would do with him whatever She may.
- PS to last post….here is another note…..and some news about a plug day!
- Posting some of Cassie’s feelings about being confined to a chastity device….