This is a fantasy. All characters are over 18 years of age.
Compulsive part3
by sheepisheyes » Thu May 16, 2024 10:13 am
Billy was beside himself. He couldn’t believe Stacy didn’t unlock his cage. He was so miserable. The next day no one was home so he snuck into his mother’s room to see if he could find the key. He opened her dresser drawer and saw all of her wonderful panties. As he was picking them up to smell them he heard something drop and realized it was the key! This was meant to be. He got his Vaseline and stripped his clothes off and unlocked his cage. Oh, what a wonderful feeling to have his cock free. He found a dirty pair in the hamper and put them over his head, so the crotch was on his nose and mouth. What a powerful sexy smell. Then he pulled a pair pink panty’s up his legs. The silky feel on his cock was wonderful. His balls fell out either side as he pulled them up tight, so it encased his cock. Then he started stroking.
Meanwhile his mother arrived home. He heard the garage door open but couldn’t stop, this was his only chance. He didn’t care if she caught him. And catch him she did. Nancy heard the telltale wanking sounds and walked up stairs. Billy hadn’t even bothered to close her bedroom door. He heard his mother coming and knew he was about to get caught but couldn’t stop. He needed to get caught. There was her son laying on her bed with a pair of her pink panties on and another pair over his face and head. She stood there and took in the scene. “Billy! How did you get out of your cage? What are you doing in my panties?” In a muffled voice Billy said, “I’m sorry. I have to play with myself. That’s all I want to do! I hate that cage!” She watched as he flooded her panties with cum. She could see the wetness spread through the pink fabric as he convulsed over and over.
She laid on the bed next to him and lifted up the panties to see his hand still around his cock but strands for sticky cum all over the inside of her panties. It was a huge explosion of cum. Billy started crying “Oh mommy please don’t put me back in that cage. I hate it so much. Please let me be a masturbator.” She pulled Billy close so that his head was between her enormous breasts. “Oh, Billy you poor thing. Alright we won’t put the cage back on you” she told him. “Really mommy! Oh, mommy thank you so much”. She felt his hand start to move inside the cum filled panties. His tempo increased and she pulled his head deeper into her cleavage. He let out a big sigh as his body gently spasmed and added another huge load to the already cum soaked pink panties. She pulled her panties off his head and Billy stood up. He looked ridiculous in the panties. His balls dangling out the sides and the buckets of cum soaking through them.
Billy was on top of the world. The whole family noticed how much happier he was now that he could masturbate freely. He was smiling and greeting everyone then running up to his room and playing with himself. Everyone agreed it was better than locking him up and making him miserable. Billy embraced that he was a masturbator and so did his family. He didn’t bother closing his door anymore and didn’t deny that he jerked off all the time. His sisters humiliated him more than before because he started to get a reputation outside of the house and people started teasing his sisters. That was making them upset. Billy got bolder and started taking his sisters panties and wearing them when he played with himself. He stopped caring about being ridiculed.
“Mom this is ridiculous he keeps stealing our panties and playing with himself where ever he wants. My friends come over and he doesn’t even shut his door. He is the laughing stock of our school”. Nancy noticed this too. Billy was now not only a chronic masturbator but a sissy too. He was soiling everyone’s panties with his gallons of cum. Nancy decided to call the Dr. Brenda Wynter for some advice. She explained how the chastity cage kept him from masturbating but turned him into a horny panting puppy dog that begged all the time to be let out. How it was so annoying for everyone. Then after removing the cage, he now thinks he no longer needs to hide is addiction and spends every moment playing with himself and doesn’t try to hide it. He also has taken to wearing panties. “Oh my” Dr Wynter said. “You say he has started wearing panties? I didn’t foresee the sissy side in him. I fear there are only a few choices. You can consider castration or sissification. Castration will take care of the problem, but it is a bit extreme. It would remove all libido and any desire to masturbate would be gone, Billy would be a docile wimpy boy. Sissification would not eliminate his masturbation, but it might make it easier to deal with, especially in a house full of women. He would have his own panties and only be allowed to masturbate when wearing his panties. This would be sufficient humiliation to entice him, and soon he would only want to masturbate in his panties. He would become a docile obedient sissy.” Beverly told her. Nancy said, “Well let’s try sissification and if that doesn’t work we’ll castrate him”.
“Billy we have some new rules around here” His mother said as she walked into his room carrying bags of panties and dresses. “These are for you” Billy’s eyes lit up when he saw all of the panties as well as his boner. “What are the dresses for?” he asked. “You will be wearing those as well as the panties and you are only allowed to masturbate while wearing them. You can masturbate all you want but you must be wearing panties and a dress and ask permission.” “Oh, mommy that’s all I want. I will be happy to do that” he answered. “You will need to obey us from now on and if you do you may masturbate as much as you want”. “Yes mommy I promise to obey” he replied gleefully.
The sisters were informed of the new arrangements, and they all clapped when Billy came down the stairs in a fluffy short dress and ankle socks. “Oh, Billy you look so pretty!”. Billy blushed and even curtseyed. They all started giggling. “Did you wear your panty too?” Billy lifted up his dress to show his frilly pink panties. The bulge was very pronounced, and they all could tell he would be playing with himself any minute. “Billy you look a little excited. Is there something you want to ask us?” Stacy said. “Would it be ok if I played with myself” he said in a lispy voice. They all laughed at the transformation. “Of course, you may. Run upstairs and play with yourself in your room and keep your panty and dress on!” Stacy said. “Oh, thank you so much. I promise I will.” Billy said and ran up the stairs, his dress bouncing and showing his cute little panties. They all laughed as they watched him go.
“Well, he’s taken well to his new role. We didn’t know he would be such a good sissy.” Stacy commented. “I think it’s just what he’s been looking for. Billy needs to be controlled and humiliated. That seems to be what excites him the most.” Nancy told the girls. Billy came down the stairs red faced and smiling. “Did you have fun Billy?” his little sister asked. “Oh yes I did! Margret” Billy replied. Stacy said, “Let’s see your panty Billy”. Billy came over to them and lifted his dress. The pink panties were all wet and sticky with cum. “Would you like to change your panty Billy?” Stacy asked. “Oh no Stacy I love the feeling of my sticky panty. I reminds me of the sissy I am.” Billy proudly answered. They all laughed as he blushed.
It turned out Billy loved to be told what to do and his sisters loved to put him to work. The arrangement was working nicely. The one thing they realized, is that they needed to encourage his masturbation. As long as they did that he seemed to be very obedient. Laundry day was getting a bit gross. His cum soaked panties were pretty bad. He must cum in them 10 times a day and never changes them. Nancy admonished Billy for only changing them once a day. Billy asked his mother if he could be spanked. “Why on earth for Billy? Have you been naughty?” she asked. “Because of my dirty panties” he said as he hung his head. “I think you like the idea of being spanked don’t you?” she asked. “Yes mommy I do, but I deserve it too.” he replied. “Very well. I think I will let your little sister Margret spank you then.” Billy thought about how humiliating that would be and got hard under his dress. “As you wish mommy” he said.
They stood in the living room and Margret told Billy to hold up his dress. She reached in and touched his cum soaked panty. “Gosh I can see why you are getting a spanking. These are soaked!” She slid his panty down and strings of cum stuck to his cock and balls and to the panty. It was a cummy mess. She told him to bend over and began to spank him. Her little hand not doing much damage, but the act and the humiliation was enough. After 20 smacks Billy stood up and his cock has pointing straight out, he obviously enjoyed the spanking. Margret just stared at the giant penis. “Mommy can I make him squirt? I’ve never made a boy quirt before”. Nancy thought about it and said, “Sure but put a towel down to stop the mess” Billy spread his legs a little, so his balls were dangling in midair. Marget’s hand grasped his cummy shaft. She didn’t need lube since there was such a cummy mess. Her hand looked tiny grasping his shaft. Her fingers tips wouldn’t touch around its girth. She slid her little hand up and down “Am I doing it right?” she asked. “Yes dear but grab a hold of his scrotum with your other hand”. Her little hand slid up and down Billy’s cock and her other hand gently squeezed and released his balls. Her hand was so small the sensation was very different. His balls were huge in her hand and draped over the sides. “I think he’s going to squirt! Look at his Trump face and I can feel him getting fuller. Sure enough, he exploded as he held his dress up so as to not get it messy. He looked hilarious standing there holding his dress up, thrusting his hips as his hard cock shot sperm into the towel on the floor. “That’s a good sissy!” Nancy said.
His mother brought home her date. A large muscular black man, Tyrone. He was at least 6’8” and an appropriate 250lbs. Nancy couldn’t wait to bring him to bed. She told him about Billy wondering how he would react. He laughed saying he would like to meet the little sissy white boy. They sat on the couch and Billy came down the stairs wearing a puffy pink short dress, black MaryJane’s and white ankle socks. She curtsied for them. “Billy this is Tyrone”. “Hello Mr. Tyrone, I am Billy the sissy”. Tyrone noticed the bulge under his dress. “Billy looks excited” he laughed. “Billy show Tyrone your panty”. Billy lifted his dress, and his huge cock was straining against the silk panty. “My goodness he is very large for such a young age, I would have pictured a sissy with a tiny little penis”. “Billy show Tyrone your penis”. Billy pulled down his panty and out popped his manhood. “I bet he’s bigger than you” Nancy teased. Tyrone said, “We’ll just have to see” and pulled down his pants exposed a very large but not yet erect penis. “Well, that is impressive, I think Billy is bigger right now. Billy make Tyrone hard.” Billy kneeled in front of him and grabbed his cock. He started stroking it and soon it came to life. Billy was amazed, it really was larger than his and the balls were huge as well. He was mesmerized as stroked it. Nancy and Tyrone watched in humor as Billy stroked and stared. “Would you like to suck him Billy?” “Oh yes mommy can I please? Will he cum in mouth?” Billy asked. Nancy looked at Tyrone “Can you recharge for later and have any left for me?” “Most certainly “he replied. Billy lowered his head and engulfed Tyrone in his mouth. It felt hot and salty in his mouth as he bobbed his head up and down, wondering when it was going to explode. He placed his hand under the giant balls and massaged them.
Billy got his wish as Tyrone emptied his seed into little Billy’s waiting mouth. “Hmm” he moaned as Tyrone placed his hand on Billy’s head and pushed his cock deeper down his throat. Poor Billy gagged a little as he swallowed blast after blast of cum. The salty warm liquid coursing down his throat. When Tyrone was done Billy lifted his head as a string of cum dirpped down his chin. Nancy looked at him and said “What a good sissy! Now you really are a full-blown sissy. How did you like your first taste of a real man’s cum?” Billy answered with a big smile on his face “It was wonderful. I hope I can do it again soon”.
Lynne was sitting on the couch talking to her friend. “I asked my boyfriend Evan if I could sit on his face, and he wouldn’t let me.” Her friend replied “Oh that stinks, I sit on Todd’s face all the time. I love to rub my pussy all over his face until I cum. He loves it too.” “You are so lucky! I want to do that so bad”. Billy overheard this conversation. Later that evening he approached Lynne and said, “I know it’s not the same as Evan but you can sit on my face if you want to”. Lynne looked surprised “Where you listening to my conversation earlier?” “I didn’t mean to. I just heard that part.” Lynne thought about it. “Ok. Go to my room and lie down on the floor”. Billy ran upstairs to her room. Billy was lying prone on the floor looking up eagerly. He had his cut yellow Buffon dress on. Lynne pulled her panty off from under her little skirt and stood over Billy’s face. Billy looked up at her hairy pussy. It looked damp and the smell he realized he had smelled before, arousal. “Stick out your tongue and lick me as a ride across your face. I am not going to sit still I am going to rub my pussy and ass from your nose to your chin until I cum all over your face.” She told him. “Please do! That sounds perfect. Use me like the sissy I am.” He replied.
She started sliding her pussy over his face. His tongue went from pussy to asshole, his nose would be engulfed in her pussy then smelling her ass. She started getting wetter and the sloshing sounds got louder. Billy pulled up his dress and grabbed his cock out of his purple panty. He was rock hard and started stroking. Lynne with lust in her eyes watched his fat cock pointing in the air as she violently rode his face. Like her mother, it was just too much, seeing that huge cock. She knew it was taboo and she shouldn’t, but she lifted off his face and plunged her wet pussy onto his throbbing cock pushing his jerking hand out of the way. Billy gasped as she started fucking his cock. The sloshing sounds got louder as her pussy lubricated itself. The warm pussy on Billy’s virgin cock felt amazing. His balls and cock swelled even more. Lynne felt him getting bigger and started pounding her pussy onto his cock harder. Slapping into his swollen balls. Suddenly Billy exploded and Lynne felt the warm sperm splashing into her womb. She kept fucking him and feeling each spurt of cum deep inside her. She knew this was taking a huge risk, but it felt so good she couldn’t stop herself. She pulled off his cock with a plop and moved back over his face. “Suck all the cum out quick! “and down she went over his mouth. Billy tried and a lot of cum came out, but he didn’t get all of it as it ran down his face.
Nancy found out about Billy and his sister. “I cannot believe you fucked your sister!” she yelled at him. “Mom! I didn’t she climbed on top of me. She was sitting on my face then climbed over and sat on my penis”. “What do you mean sitting on your face?” She asked. Billy explained to his mother how his sister’s boyfriend would not let her do that and Billy offered his face. “She just sits on your face?” “No mom she grinds herself all over my nose and mouth until she is all wet and its dripping down my face” he told her. Nancy felt a tingle. She though to herself Tyrone would never let me do that, he is too much of a man. But it does sound intriguing. “Either way that penis of yours is too dangerous in this house full of women. It is just too easy to take advantage of a sissy. Especially with that giant cock of yours. I’m sorry but I think you are going to have to be castrated” she told Billy. “What does that mean?” Billy asked. “They will remove your testicles.” She answered. “Wwwwhat! No please mom No!”. “I’m sorry Billy but we cannot have you getting your sisters pregnant. Once your testicles are removed you will not want to masturbate anymore. You’ll be the perfect sissy.” “But I love to masturbate! That’s all I want to do. I can still be the perfect sissy and masturbate”. “I know Billy, but you will still be allowed to please us orally if we wish but we just cannot risk pregnancy. I know you do not know how to fornicate like a man but the temptation to sit on that hard cock is too great. Plus the amount of sperm you produce is extremely dangerous. The decision is final Billy. I would suggest you masturbate as much as you can until then”.
Dr Wynter was going to perform the castration. Billy dressed in his prettiest pink dress and panties. He was so sad to be losing his balls, but he accepted the situation and wanted to be the best sissy he could be. They laid Billy on a table and lifted his dress and removed his panties. Both women just looked at his massive cock and balls with a sadness. Dr Wynter said “Now Billy I need to hook you to a milking machine to remove as much sperm from you as possible before we remove your testicles. You will find this very enjoyable” She slid the milker onto his penis and turned it on. It started messaging his penis and created suction. Dr Wynter fondled the huge balls to stimulate them. Before long Billy wash gushing cum into the milker as they watched the white fluid being captured. She kept the machine running for 30 more minutes after the first ejaculation. Billy was in total bliss. His legs splayed open and his head back and the last time he would be making his Trump face. Before he was out of his orgasm she injected him with anesthesia and Billy passed out. She grabbed her scalpel and popped out his huge testicles one at a time. He was stitched up and sent home.
Billy really did become the perfect sissy. His voice got higher, and he started to look more and more feminine. He no longer got boners and his missing balls allowed him to fit much better in his panties. He became docile and loved being a maid to his sisters. He was just adorable. Luckily his sister did not get pregnant and now there was no worries about that. The older sisters and his mom were using his mouth and face quite often and Billy loved it. He missed his balls and playing with himself, but he also had no desire other than to please others and not himself.