Laughing at my little cock trying to get hard
The older woman next door had caught me dressing up. She seemed so supportive, telling me it was nothing to be ashamed of and that I looked sexy in my feminine clothes. Soon she had invited me over to her house to dress up for her. Quickly discovering that humiliation made me hard, she began to take me out shopping, eventually making me try on panties and lingerie for the sales girls, and once for another man. When we came home from that she let me masturbate as she watched and smiled.
One day when I went over she handed me a wrapped box and said she had bought me a present. I opened it and stared in shock at a very small chastity cage. Smiling widely, she told me how exciting it would be if I locked my little cock up, how it wouldn't be able to get hard and "tent" out my pretty panties, how much more excited and aroused I would get which would make my next orgasm that much more intense. She had always been so supportive and helpful in feminizing me, and it had been almost two weeks since I had cum. I quickly agreed and very soon she had me locked in the cage. It was very small, crushing even my tiny cock.
As soon as she had my cock locked away her whole demeanor changed. She pulled off her clothes, spread her legs and demanded that I worship her old pussy. I had not had any interest in her sexually, but somehow I found myself on my knees, leaning forward, my face between her chubby thighs, licking her pussy. "Mmmmmm" she moaned, "Sissy boys make the best pussy lickers." She took several orgasms from my tongue before standing, turning around, bending over and commanding me to worship her ass. I hesitated and she snapped, "Now you sissy little bitch." Her words and the humiliation of what I was about to do shot directly to my cock and I winced in pain as it tried to get hard. Leaning forward I spread her saggy cheeks and gave her a long deep kiss directly between them. I spent the next half hour kissing and licking and worshiping her big saggy ass. Finally she stepped away, patted me on the head, laughing at my little cock trying to get hard in the cage and sent me home.
Every day for the next week she would dress me in something pretty and make me please her. She trained me in what she enjoyed, using my lips and tongue on her breasts, her pussy and her ass. Enjoying my hands running over her naked body and my fingers in her pussy to make her cum. She even took me out to an adult shop with a bustier, stockings and panties on under my clothes to buy a strap on, completing my humiliation by telling the creepy old man behind the counter that it wasn't for her to us on me, as I am sure he thought, but for me to use on her. "You see" she laughed, as I was paying the man, "He is a cute feminized sissy boy with a very tiny cock that I had to lock in a chastity cage. But with this I can pretend he is a real man and let him fuck me." I was mortified, but she knew full well that I was also incredibly aroused.
Finally, after a week, I asked her to please unlock me and let me cum. She just laughed. "Silly little bitch" she smiled. "You should have asked how long I intended to keep you in chastity. An orgasm once a week? Don't be silly. That would never give you enough time to get all desperate and frustrated. No, my pretty sissy bitch, you are going to be locked up for much more than a week. I can safely say even much more than a month. I am going to enjoy seeing how far I can push you, what kinds of humiliating and demeaning things you will be willing to do to get out of that cage and wank your silly little cock. Just thinking of what I am going to make you do is exciting me. Get your pretty little mouth over here and take care of that."
As I was on my knees licking her wet hairy pussy I felt her hand on my head. "What a good girl" she said, her use of the feminine pronoun sending a shiver through my cock. "Do a good job sissy, once you please me properly we are going shopping again. Now that you know the truth about your chastity it is time to go buy you skirts and dresses and pretty tops. You will look so sweet when I take you back to the adult shop and show you off to that creepy old man. Who knows, if you are a very good sissy I may even let you pull up your skirt to show him your cute tiny cock in its cage." Looking up into her eyes, my cock hard and pinched in my cage, my face wet and shiny from her pussy I simply said, "Thank you Mistress, I will be a very good sissy."
One day when I went over she handed me a wrapped box and said she had bought me a present. I opened it and stared in shock at a very small chastity cage. Smiling widely, she told me how exciting it would be if I locked my little cock up, how it wouldn't be able to get hard and "tent" out my pretty panties, how much more excited and aroused I would get which would make my next orgasm that much more intense. She had always been so supportive and helpful in feminizing me, and it had been almost two weeks since I had cum. I quickly agreed and very soon she had me locked in the cage. It was very small, crushing even my tiny cock.
As soon as she had my cock locked away her whole demeanor changed. She pulled off her clothes, spread her legs and demanded that I worship her old pussy. I had not had any interest in her sexually, but somehow I found myself on my knees, leaning forward, my face between her chubby thighs, licking her pussy. "Mmmmmm" she moaned, "Sissy boys make the best pussy lickers." She took several orgasms from my tongue before standing, turning around, bending over and commanding me to worship her ass. I hesitated and she snapped, "Now you sissy little bitch." Her words and the humiliation of what I was about to do shot directly to my cock and I winced in pain as it tried to get hard. Leaning forward I spread her saggy cheeks and gave her a long deep kiss directly between them. I spent the next half hour kissing and licking and worshiping her big saggy ass. Finally she stepped away, patted me on the head, laughing at my little cock trying to get hard in the cage and sent me home.
Every day for the next week she would dress me in something pretty and make me please her. She trained me in what she enjoyed, using my lips and tongue on her breasts, her pussy and her ass. Enjoying my hands running over her naked body and my fingers in her pussy to make her cum. She even took me out to an adult shop with a bustier, stockings and panties on under my clothes to buy a strap on, completing my humiliation by telling the creepy old man behind the counter that it wasn't for her to us on me, as I am sure he thought, but for me to use on her. "You see" she laughed, as I was paying the man, "He is a cute feminized sissy boy with a very tiny cock that I had to lock in a chastity cage. But with this I can pretend he is a real man and let him fuck me." I was mortified, but she knew full well that I was also incredibly aroused.
Finally, after a week, I asked her to please unlock me and let me cum. She just laughed. "Silly little bitch" she smiled. "You should have asked how long I intended to keep you in chastity. An orgasm once a week? Don't be silly. That would never give you enough time to get all desperate and frustrated. No, my pretty sissy bitch, you are going to be locked up for much more than a week. I can safely say even much more than a month. I am going to enjoy seeing how far I can push you, what kinds of humiliating and demeaning things you will be willing to do to get out of that cage and wank your silly little cock. Just thinking of what I am going to make you do is exciting me. Get your pretty little mouth over here and take care of that."
As I was on my knees licking her wet hairy pussy I felt her hand on my head. "What a good girl" she said, her use of the feminine pronoun sending a shiver through my cock. "Do a good job sissy, once you please me properly we are going shopping again. Now that you know the truth about your chastity it is time to go buy you skirts and dresses and pretty tops. You will look so sweet when I take you back to the adult shop and show you off to that creepy old man. Who knows, if you are a very good sissy I may even let you pull up your skirt to show him your cute tiny cock in its cage." Looking up into her eyes, my cock hard and pinched in my cage, my face wet and shiny from her pussy I simply said, "Thank you Mistress, I will be a very good sissy."
2 years ago
