Ch. 02
Lisa watched TV as John went online. She was hoping he would fully understand and accept becoming a sissy cuckold. The freedom of been able to fully dress and masturbate as a female while his wife goes out to dinner with a co-worker. She really got excited thinking of going to that restaurant for dinner and dancing with Troy and liked the idea of spending a nice evening with dinner and maybe dancing with a good looking black man, even if it was only companionship he was after. After about an hour she went to check on John and found him deep in thought, with his hand on his cock.
"Oh oh oh! Is my sissy all excited again?"
He said "Lisa, it does seem to happen a lot. A lot of cuckolds are sissies it seems, and more and more men are wearing sexy satin and lace underwear. Even suspenders and stockings, and their wife helps them!"
Was he asking her for help?
"Yes darling, I told you so. It’s quite normal now for a lot of couples, and from the stories I read they both get so much better sex. Even our sex has gone up a notch since Troy wants to take me on a date to that beautiful restaurant. Let’s go to bed darling, I have surprises for you and you owe me a licking."
"Lisa, by accident I came across a stranger online."
"Darling what do you mean?"
"I don’t know how it happened but this small window opened and someone wrote 'Hello there! Can I please chat with you?' I have no idea how he got my number."
"John, you are not very computer literate. He did not have your number. It was a chat online messenger from the site you were on. So what did he say then John?"
"He asked me if I was a cuckold like him, or a female. I said male. Then he asked me if I liked the stories about sissy cuckolds. I said yes but I was not a cuckold. He asked me if I was sure about that. Then, Lisa, he asked me if I was a sissy and I could not stop from saying yes. He asked if I was married and I said yes. He asked if you knew that I'm a sissy I said yes she does. He said 'Oh you are so lucky!'
"He asked if you were going on dates with other men. I said no, but a man has asked you out at work. 'Oh that’s nice! And when is she going?' I told him I didn't approve the date yet."
"What did he say then, John darling?" Lisa asked, as she slowly stroked his bulge.
"He told me there is no harm in letting you go out if it makes you happy, so I should let you go on date with your friend from work, and I should buy you a nice dress and new lingerie. He said his wife has been going out on dates for the past year and he is a sissy too, and loves to get dressed in lingerie while his wife is on her dates. Their sex life has improved greatly, and he said he loves to help his wife get dressed for her date. When you came in I cut him off. Sorry, I was shy that you might want to chat with him."
"Oh my little darling girl! You see now that it's very common. Let’s go to bed darling girlfriend, I have to dress you. We also need to look after this hard cock again. You are getting so horny since we talked about Troy! Come on, maybe you can go on that site tomorrow and he might be there again. You will have to apologize for cutting him off, and have a good chat with him."
Lisa took John to the bedroom and told him to strip. He was all excited and really hard.
"Lisa, I noticed tonight that most cuckolds are sissies in the stories. Even the man that chatted with me was a sissy."
"Yes John, because a real sissy like you loves to dress up and be a girl, and they like their wife or girlfriend to have time with another man. They understand, as they themselves are girls. They like their wife to be out at night so they can play at being a girl and dress up, knowing their wife is busy and won’t be home for hours. They can put on miniskirts and dresses and masturbate dressed as a woman. Now John, let's put this lovely black suspender belt on you. You've put it on often enough that you can do it yourself. Come on, don’t be shy!"
John stood up, and he felt a little shy about it but he put it on easily. His cock sticking out hard. "Oh darling, your becoming such a girl. That's lovely on you! I got you the 8 strap belt it’s much more slutty. Now slide up these stockings and let’s both help to clip them on." The stockings were put on, and they both thought they were really a lovely shiny black light mesh. So sexy.
"Now darling, they look beautiful on your girly legs but wait we have more! Now this bra."
"Oh Lisa, I can’t wear a bra. I don’t have breasts."
"Well John, you do have budding breasts and I have a fix for that. Now here, let me help you girlfriend."
Lisa put the bra on and it fitted perfect. The breasts were there, but quite small as yet. She took two silicone falsies from the bag and as John watched she fitted them into the bra, giving John lovely D size breasts, with a lovely full shape. Each had a false nipple.
"Now your knickers. John, when you are playing and having fun dressed up like this while I'm out, you must always lower your knickers and put this hand towel on your tummy and under your cock so you cum on the towel and not on your lovely knickers, do you understand baby?"
"Yes. Lisa."
"Good girl, no wet knickers then! Do you feel so nice, John?"
"Oh yes darling, it’s unbelievable. I cannot deny I feel such a girl. Do I look silly, Lisa?"
"Oh god no, you look such a girl, especially your breasts. Do you like your breasts?"
"Yes Lisa, they are so realistic! Lisa, the tablets you are giving me... Will they make my breasts bigger?"
"Oh yes John, so much bigger in time. Slow but sure, and they'll give you girly hips as well. Will you be happy then, darling?"
"Yes Lisa, I like them now."
Lisa started rubbing his breasts as John was masturbating gently.
"Go nice and slow, baby. Take it easy and enjoy being a girl like me. You are beautiful like me baby. That’s what Troy said, that I'm beautiful. Do you agree, darling?"
"Oh yes Lisa, you are so beautiful. I want you to look beautiful Lisa, always."
"Troy will want me baby, when I look so beautiful. John, I will get myself matching underwear with your set. I like them so much. We will be like twin girls then!"
"Please do Lisa, I want you looking so sexy too!"
"But John, you won't be allowed to play with my new lingerie. They are for special occasions only, like going out with Troy."
Lisa was now ready to start testing John.
"Oh oh oh! Is my sissy all excited again?"
He said "Lisa, it does seem to happen a lot. A lot of cuckolds are sissies it seems, and more and more men are wearing sexy satin and lace underwear. Even suspenders and stockings, and their wife helps them!"
Was he asking her for help?
"Yes darling, I told you so. It’s quite normal now for a lot of couples, and from the stories I read they both get so much better sex. Even our sex has gone up a notch since Troy wants to take me on a date to that beautiful restaurant. Let’s go to bed darling, I have surprises for you and you owe me a licking."
"Lisa, by accident I came across a stranger online."
"Darling what do you mean?"
"I don’t know how it happened but this small window opened and someone wrote 'Hello there! Can I please chat with you?' I have no idea how he got my number."
"John, you are not very computer literate. He did not have your number. It was a chat online messenger from the site you were on. So what did he say then John?"
"He asked me if I was a cuckold like him, or a female. I said male. Then he asked me if I liked the stories about sissy cuckolds. I said yes but I was not a cuckold. He asked me if I was sure about that. Then, Lisa, he asked me if I was a sissy and I could not stop from saying yes. He asked if I was married and I said yes. He asked if you knew that I'm a sissy I said yes she does. He said 'Oh you are so lucky!'
"He asked if you were going on dates with other men. I said no, but a man has asked you out at work. 'Oh that’s nice! And when is she going?' I told him I didn't approve the date yet."
"What did he say then, John darling?" Lisa asked, as she slowly stroked his bulge.
"He told me there is no harm in letting you go out if it makes you happy, so I should let you go on date with your friend from work, and I should buy you a nice dress and new lingerie. He said his wife has been going out on dates for the past year and he is a sissy too, and loves to get dressed in lingerie while his wife is on her dates. Their sex life has improved greatly, and he said he loves to help his wife get dressed for her date. When you came in I cut him off. Sorry, I was shy that you might want to chat with him."
"Oh my little darling girl! You see now that it's very common. Let’s go to bed darling girlfriend, I have to dress you. We also need to look after this hard cock again. You are getting so horny since we talked about Troy! Come on, maybe you can go on that site tomorrow and he might be there again. You will have to apologize for cutting him off, and have a good chat with him."
Lisa took John to the bedroom and told him to strip. He was all excited and really hard.
"Lisa, I noticed tonight that most cuckolds are sissies in the stories. Even the man that chatted with me was a sissy."
"Yes John, because a real sissy like you loves to dress up and be a girl, and they like their wife or girlfriend to have time with another man. They understand, as they themselves are girls. They like their wife to be out at night so they can play at being a girl and dress up, knowing their wife is busy and won’t be home for hours. They can put on miniskirts and dresses and masturbate dressed as a woman. Now John, let's put this lovely black suspender belt on you. You've put it on often enough that you can do it yourself. Come on, don’t be shy!"
John stood up, and he felt a little shy about it but he put it on easily. His cock sticking out hard. "Oh darling, your becoming such a girl. That's lovely on you! I got you the 8 strap belt it’s much more slutty. Now slide up these stockings and let’s both help to clip them on." The stockings were put on, and they both thought they were really a lovely shiny black light mesh. So sexy.
"Now darling, they look beautiful on your girly legs but wait we have more! Now this bra."
"Oh Lisa, I can’t wear a bra. I don’t have breasts."
"Well John, you do have budding breasts and I have a fix for that. Now here, let me help you girlfriend."
Lisa put the bra on and it fitted perfect. The breasts were there, but quite small as yet. She took two silicone falsies from the bag and as John watched she fitted them into the bra, giving John lovely D size breasts, with a lovely full shape. Each had a false nipple.
"Now your knickers. John, when you are playing and having fun dressed up like this while I'm out, you must always lower your knickers and put this hand towel on your tummy and under your cock so you cum on the towel and not on your lovely knickers, do you understand baby?"
"Yes. Lisa."
"Good girl, no wet knickers then! Do you feel so nice, John?"
"Oh yes darling, it’s unbelievable. I cannot deny I feel such a girl. Do I look silly, Lisa?"
"Oh god no, you look such a girl, especially your breasts. Do you like your breasts?"
"Yes Lisa, they are so realistic! Lisa, the tablets you are giving me... Will they make my breasts bigger?"
"Oh yes John, so much bigger in time. Slow but sure, and they'll give you girly hips as well. Will you be happy then, darling?"
"Yes Lisa, I like them now."
Lisa started rubbing his breasts as John was masturbating gently.
"Go nice and slow, baby. Take it easy and enjoy being a girl like me. You are beautiful like me baby. That’s what Troy said, that I'm beautiful. Do you agree, darling?"
"Oh yes Lisa, you are so beautiful. I want you to look beautiful Lisa, always."
"Troy will want me baby, when I look so beautiful. John, I will get myself matching underwear with your set. I like them so much. We will be like twin girls then!"
"Please do Lisa, I want you looking so sexy too!"
"But John, you won't be allowed to play with my new lingerie. They are for special occasions only, like going out with Troy."
Lisa was now ready to start testing John.
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