It was 6:30 in the afternoon when Lisa got home from work. I get home earlier because my job is not as long in the day as hers. I had dinner ready when she got home, so I told her to sit down and relax while I served up her meal. I enjoyed cooking dinner for her. We both work hard but I have that spare extra few hours. Lisa often jokes and says I’d make a great wife for some man someday as I’m such a good cook and I help around the house with the cleaning, the washing the ironing etc; Well, we both share as we are both working. Lisa sat down and I poured her a nice glass of wine and we chatted away.
After finishing dinner and her second glass of wine she said, "You're not gonna believe what happened today at work."
"Oh? Tell me."
"Well John, remember I told you that I got a new manager? Troy is his name."
I said "Yes, I remember you telling me about that some time ago. A black man?"
"Yeah... well Troy is lovely really. He’s been very kind to me and he's helped me on many occasions. Today we were having coffee in the canteen at lunch and he asked me if I like to go out with him for dinner some evening. Maybe this weekend. I couldn’t believe, it, he was so shy and embarrassed. I asked him if he forgot that I was married and he was all apologetic, but he was so nice about it. I said I loved the idea and thanked him for the offer but that I didn’t think my husband would approve of my going on a dinner date with somebody from work.
"He said, 'Oh that's a pity. If your husband would ever let you have a special night out, the offer is always open.'
"I replied, 'I don’t think so Troy but thanks!'
"John, I was really shocked! The moment was a bit awkward, but I will say he’s a lovely man. He’s good looking and so nice, but I’m married so he understands and that’s the end of it. I was wondering if he saw the rings on my fingers. My wedding ring and engagement ring, but he didn’t or maybe he did and chose to ignore it. It was bugging me John, so later on in the afternoon I just asked him about it.
" 'Troy, did you not see the rings on my fingers? Didn't you know that I was married?'
" 'I saw them, but nowadays that'st a great indicator because there are so many people divorced, separated, or living apart that you can't be sure that the person is free or not. Or maybe you're living in an open relationship, or you're a hot wife and your husband is a cuckold or even a sissy cuckold, which is very common these days. Lisa, just forget it. I’m sorry, I shouldn’t have asked you out for dinner. I should have accepted that the rings on your fingers meant you were married and that was it. Don't worry about it. you're married, you're not in an open relationship so that's the end of it. You're just so beautiful I had to take the chance that you might say yes.'
"I said 'Thank you Troy, for the lovely compliments!'
"Lisa, what did Troy mean by 'hot wife and cuckold' or 'sissy cuckold'? I don’t understand what that means."
"Oh John, I wasn’t sure either. I have heard about the word cuckold but I wasn’t sure, so in the afternoon when Troy went out for a while I looked it up on the office computer. I searched the internet and was so amazed John! A cuckold, John, is a husband who gets very excited and horny when his wife is with another man, be it just dating him or actually having dinner with him. A sissy cuckold is a husband who loves the feeling of the silky underwear that women wear, and he dresses up feminine. A sissy loves silky sexy lingerie, he loves to wear suspenders, stockings, panties, things like that. Maybe a silky, girly nightie in bed. A lot of men have a feminine side that comes out when dressed in lingerie. It’s lovely!
"Also, the cuckold apparently loves to dress his wife for her dates. He buys her new dresses and sexy underwear to wear for her date, as he is so proud of her and wants her to be sexy. All that sort of thing. It’s not always sexual. It can be just a exciting evening out, like dinner and dancing.
"So a hot wife is a woman, either wife or girlfriend, who has a boyfriend or husband who is a cuckold. He wants her to date other men, he gets off thinking of his wife out with other men, he wants his wife to be happy. That makes him very excited. He gets so much excitement he wants it to happen regularly. She has his permission and approval to go out with other men for dinner, and she herself wants to go out with other men, even if it's just dinner and dancing."
"But Lisa, would you like to go out with another man like in the stories you read?"
"Well John, it was very exciting to be asked out I must admit! Especially being married. It was a great compliment to us. I didn’t know the full extent of cuckolding but I was amazed when I read about it. It has such a broad range and it sounds very exciting for those involved. John I think you should read some stories yourself, just to see what he was talking about. It’s amazing! I didn’t think it was so commonplace in relationships, especially marriage relationships, but apparently it is very common and even in boyfriend girlfriend relationships. Troy must know all about it and he thought we might be like that. Anyway it’s actually so funny that he asked me out on a date! At least it was a dinner and dancing date and not as a hot wife. I felt sorry for him."
"Why would you feel sorry for him?"
"Because he’s only moved here a few weeks ago. He doesn't know anyone and also the fact that he is coloured. I suppose he just wanted some company, and he chose an exceptionally beautiful woman like your wife!" She giggled.
After dinner we sat in the front room. While Lisa watched TV I decided to go online and check out this cuckolding thing. Lisa joked and asked me if I wanted to be a cuckold, and I told her I just wanted to understand it a bit better and see if it's for real.
"Oh John, it happens and it’s big! Especially the sissy stuff. So check it out, there are some very exciting stories."
"It was easy to find information about cuckolding and even sissy cuckolds. I was amazed at how many search results I got and not sure where I should start. One story stood out, an account from a sissy cuckold about his first time experience. It was an interesting story, and I soon had a huge, rock hard erection. WTF? Why was I so hard?
It was very exciting. The husband became a sissy, and then he got excited thinking of his wife with another man. There was one part that I really related to. You see, sometimes if Lisa is away or working late I will masturbate. I love to massage my cock with Lisa’s silky panties, especially the satin and lace ones, or even her silky nightie. Rubbing it all over my lower half, it feels lovely and makes my cum stronger and more exciting. I never considered that I was a sissy, but in the story I was reading it was how the husband started. His wife knew he was using her lingerie but she didn't say anything. She loved it. When it came out in the open, she encouraged him to dress for bed with panties and nightie and they were like two girls together in bed.
Then it went on about a friend taking her out with her husband’s approval. He got so excited she went on a date with this friend, and the story was all about him becoming a sissy cuckold and her having sex with this friend and how exciting the whole situation became for them. It was a really hot story and I had my hand on my bulge, caressing it. I saw Lisa was standing in the door, watching me touch myself.
She said "It’s ok baby. You look so horny! I am so happy for you baby." She looked at the screen. "That looks familiar John. It’s the same story I read! it’s so hot. He loved being a sissy and a cuckold. Now, John, I can tell you at last. Like this story I know that you have used my lingerie to masturbate when I am out. I never said anything as there was no harm. John, sometimes I masturbate also, so it’s ok babe."
Then Lisa put her hand on my bulge and squeezed me. Her fingers opened my pants, she took my cock out and suddenly her head was in my lap sucking my hard cock. Lisa just adores sucking cock. Now I don’t have a very big cock. Average, I would say, at about five inches. Lisa never complained and she was loving it now as she sucked hard on me.
"Let’s go to bed, darling, and finish this. I am very horny and I want your cock in me. Come on, let’s go!"
Lisa was super horny, and so was I. She laid me on my back and started to caress me with the panties she had just taken off. I was so hard and excited I moaned.
Lisa said "Oh my. You love my panties, don’t you baby?"
"Oh fuck Lisa, I am so close."
"Wait now baby, don’t you dare cum yet! Let’s chat and play for a while. I want to enjoy these new feelings and openness, now that we both know you are a lingerie sissy girl!"
Lisa's head came to my cock and she kissed it, caressed it and rubbed it with her panties. She surprised me when she slipped the panties up my legs and pulled them on me, saying "Now that feels good babe, doesn’t it? So you are my little sissy now. Not a sissy cuckold. Just my sissy."
"Oh fuck Lisa, yes they feel lovely I must admit."
"Yes darling, you have played with them often enough to know, and I knew also!" She giggled. "So now you are coming out of the closet!" She rose up, kissing me as she took my hand and placed it over my silky covered cock. "Now babe, let me see you masturbate for me. Come on babe, don’t be embarrassed. You have done it often enough.
"I was so excited to be actually masturbating in front of Lisa, I knew I would not last long. Lisa knew it too. She stopped kissing me and said "Slowly now babe, make it last. Good. I love you in panties babe. I am going to get you your own. All men should wear silky sexy panties. I am going to make your own drawer full of lingerie for your own use. Darling, you got so excited reading about cuckolds and hotwives! I think you like the stories. You will have to read them more often, darling. I know I am. They are so exciting. I'm so glad Troy mentioned it. It’s quite common. I looked up husbands wearing lingerie and I was amazed that so many married men do. Some crossdress all the time.
"Just think darling... you letting me go out for a dinner with Troy. That would be mad!" She laughed like she had just told a funny joke. "You at home dressed in my panties and nightie, in my suspenders and stockings masturbating. It would be so exciting for the two of us! That sounds mad but so exciting! Ha ha!"
That was the trigger. I shot a load of cum in the panties as I pulled on my satin-wrapped cock. "Oh Fuckkkkkkkkk Lisa! Yes yes yes! Oh Fuckkkkkkkkk, yes yes yes oh oh oh god!"
"That’s it good girl, pull your cock. Keep cumming my baby, cum for me!"
As I slowed down, she kissed me hard then said "Oh baby, you are my little sissy. My lovely sissy. That was a huge cum, baby! You definitely need satin underwear like a sissy. The thought of me going out with Troy made you cum so hard. Admit it babe!"
"Well... Yes Lisa, for that moment when you said it, yes it did. The thought, not the fact Lisa... but he would love to take you out! Oh fuck!" The last little spasm of an orgasm hit me as I admitted it.
She said, "I know darling. I said it just to make you cum like the stories in the cuckold section on the internet. I really think reading those stories will enhance our sex life darling, especially now that we know you are a real sissy. Troy really does want to take me out as a work mate. Guess what, John?"
"What Lisa?"
"Tomorrow night you are getting into bed in panties and a nightie. We will not have any discussion about it."
"Really Lisa? Ok."
"Good girl. And tomorrow you are wearing sexy satin panties to work. I want you to feel sexy all day, baby. No more silly boxers for my girlfriend. I have always wanted you in panties, you have such a lovely girly bubble ass!"
The next day I had dinner ready for Lisa. I had a slight excitement as I remembered that Lisa was going to go to bed with me dressed in panties and nightie. I was excited all day long. Over dinner I asked Lisa how things went at work.
"Well now, John, I think you mean did Troy say anything. Yes he did. He asked me if my husband got angry when I told him about being asked out on a dinner date. I told him a little white lie. I told him you said thanks for being so complementary to his wife. He apologized again for the mistake but said the offer was still open if you would ever allow it."
"Lisa, what did you say?"
"I told him I didn't think you would allow it, but I promised to ask again. He said to tell you it would just be for the pleasure of my company and if you want to come as well, you would be most welcome. I told him that you wouldn't want to go. He requested that I at least ask you again if you would let your loving wife go to dinner with another man in a nice restaurant. And straight home again, of course!"
"Lisa he is very cheeky! He doesn't give up, and I didn't hear you saying no. You only said that I wouldn't approve. You didn't turn him down."
"Well John I did not mean it like that, but you'll never guess where he wants to take me. The Le Grande Paris!"
"Lisa, its impossible to get a booking there, and it’s so expensive! How could he afford that place? It’s the best restaurant in town!"
"I know John, and I would have nothing nice to wear to a classy place like that. You would have to buy me a new dress. If you approved for me to go, that is. He said he has a table for two booked for next Friday night and he needs someone to go with him.
"Oh John, I see you have a nice inviting bulge again! Are you as excited as I am darling? My pussy is wet from all this talk!"
Lisa knelt in front of John and opened his pants before he had a chance to say no. She pulled his hard cock from his silky panties and sank her mouth over it. She took it deep as possible, knowing she wouldn't gag as it wasn't big enough to choke her.
"Oh god Lisa! Fuckkkkkk, so good baby! What’s happening to us? Oh fuck Lisa, yes yes!"
John exploded straight into her stomach. Lisa swallowed it all and then quickly cleaned his cock before he got sensitive, then she put him back in his pants.
"Fuck Lisa, thank you for dessert! Oh baby anything for you. I love you so much!"
Lisa said "You will repay me later in bed, in your beautiful nightie and panties and lingerie I bought you. John, darling, you were so excited! I think the thought of approving me to go out - just for dinner - with Troy has you very excited! Let’s watch some TV, and then we will go to bed and play dress up, girlfriend!"
"Lisa, I'm going to read some stuff online instead."
"Good idea dear. Read the cuckold stories, but no wanking babe. That’s for later. Read more about the sissy cuckolds darling, it’s more like you yourself are. Just remember you love dressing up in lingerie and you're very feminine!"
After finishing dinner and her second glass of wine she said, "You're not gonna believe what happened today at work."
"Oh? Tell me."
"Well John, remember I told you that I got a new manager? Troy is his name."
I said "Yes, I remember you telling me about that some time ago. A black man?"
"Yeah... well Troy is lovely really. He’s been very kind to me and he's helped me on many occasions. Today we were having coffee in the canteen at lunch and he asked me if I like to go out with him for dinner some evening. Maybe this weekend. I couldn’t believe, it, he was so shy and embarrassed. I asked him if he forgot that I was married and he was all apologetic, but he was so nice about it. I said I loved the idea and thanked him for the offer but that I didn’t think my husband would approve of my going on a dinner date with somebody from work.
"He said, 'Oh that's a pity. If your husband would ever let you have a special night out, the offer is always open.'
"I replied, 'I don’t think so Troy but thanks!'
"John, I was really shocked! The moment was a bit awkward, but I will say he’s a lovely man. He’s good looking and so nice, but I’m married so he understands and that’s the end of it. I was wondering if he saw the rings on my fingers. My wedding ring and engagement ring, but he didn’t or maybe he did and chose to ignore it. It was bugging me John, so later on in the afternoon I just asked him about it.
" 'Troy, did you not see the rings on my fingers? Didn't you know that I was married?'
" 'I saw them, but nowadays that'st a great indicator because there are so many people divorced, separated, or living apart that you can't be sure that the person is free or not. Or maybe you're living in an open relationship, or you're a hot wife and your husband is a cuckold or even a sissy cuckold, which is very common these days. Lisa, just forget it. I’m sorry, I shouldn’t have asked you out for dinner. I should have accepted that the rings on your fingers meant you were married and that was it. Don't worry about it. you're married, you're not in an open relationship so that's the end of it. You're just so beautiful I had to take the chance that you might say yes.'
"I said 'Thank you Troy, for the lovely compliments!'
"Lisa, what did Troy mean by 'hot wife and cuckold' or 'sissy cuckold'? I don’t understand what that means."
"Oh John, I wasn’t sure either. I have heard about the word cuckold but I wasn’t sure, so in the afternoon when Troy went out for a while I looked it up on the office computer. I searched the internet and was so amazed John! A cuckold, John, is a husband who gets very excited and horny when his wife is with another man, be it just dating him or actually having dinner with him. A sissy cuckold is a husband who loves the feeling of the silky underwear that women wear, and he dresses up feminine. A sissy loves silky sexy lingerie, he loves to wear suspenders, stockings, panties, things like that. Maybe a silky, girly nightie in bed. A lot of men have a feminine side that comes out when dressed in lingerie. It’s lovely!
"Also, the cuckold apparently loves to dress his wife for her dates. He buys her new dresses and sexy underwear to wear for her date, as he is so proud of her and wants her to be sexy. All that sort of thing. It’s not always sexual. It can be just a exciting evening out, like dinner and dancing.
"So a hot wife is a woman, either wife or girlfriend, who has a boyfriend or husband who is a cuckold. He wants her to date other men, he gets off thinking of his wife out with other men, he wants his wife to be happy. That makes him very excited. He gets so much excitement he wants it to happen regularly. She has his permission and approval to go out with other men for dinner, and she herself wants to go out with other men, even if it's just dinner and dancing."
"But Lisa, would you like to go out with another man like in the stories you read?"
"Well John, it was very exciting to be asked out I must admit! Especially being married. It was a great compliment to us. I didn’t know the full extent of cuckolding but I was amazed when I read about it. It has such a broad range and it sounds very exciting for those involved. John I think you should read some stories yourself, just to see what he was talking about. It’s amazing! I didn’t think it was so commonplace in relationships, especially marriage relationships, but apparently it is very common and even in boyfriend girlfriend relationships. Troy must know all about it and he thought we might be like that. Anyway it’s actually so funny that he asked me out on a date! At least it was a dinner and dancing date and not as a hot wife. I felt sorry for him."
"Why would you feel sorry for him?"
"Because he’s only moved here a few weeks ago. He doesn't know anyone and also the fact that he is coloured. I suppose he just wanted some company, and he chose an exceptionally beautiful woman like your wife!" She giggled.
After dinner we sat in the front room. While Lisa watched TV I decided to go online and check out this cuckolding thing. Lisa joked and asked me if I wanted to be a cuckold, and I told her I just wanted to understand it a bit better and see if it's for real.
"Oh John, it happens and it’s big! Especially the sissy stuff. So check it out, there are some very exciting stories."
"It was easy to find information about cuckolding and even sissy cuckolds. I was amazed at how many search results I got and not sure where I should start. One story stood out, an account from a sissy cuckold about his first time experience. It was an interesting story, and I soon had a huge, rock hard erection. WTF? Why was I so hard?
It was very exciting. The husband became a sissy, and then he got excited thinking of his wife with another man. There was one part that I really related to. You see, sometimes if Lisa is away or working late I will masturbate. I love to massage my cock with Lisa’s silky panties, especially the satin and lace ones, or even her silky nightie. Rubbing it all over my lower half, it feels lovely and makes my cum stronger and more exciting. I never considered that I was a sissy, but in the story I was reading it was how the husband started. His wife knew he was using her lingerie but she didn't say anything. She loved it. When it came out in the open, she encouraged him to dress for bed with panties and nightie and they were like two girls together in bed.
Then it went on about a friend taking her out with her husband’s approval. He got so excited she went on a date with this friend, and the story was all about him becoming a sissy cuckold and her having sex with this friend and how exciting the whole situation became for them. It was a really hot story and I had my hand on my bulge, caressing it. I saw Lisa was standing in the door, watching me touch myself.
She said "It’s ok baby. You look so horny! I am so happy for you baby." She looked at the screen. "That looks familiar John. It’s the same story I read! it’s so hot. He loved being a sissy and a cuckold. Now, John, I can tell you at last. Like this story I know that you have used my lingerie to masturbate when I am out. I never said anything as there was no harm. John, sometimes I masturbate also, so it’s ok babe."
Then Lisa put her hand on my bulge and squeezed me. Her fingers opened my pants, she took my cock out and suddenly her head was in my lap sucking my hard cock. Lisa just adores sucking cock. Now I don’t have a very big cock. Average, I would say, at about five inches. Lisa never complained and she was loving it now as she sucked hard on me.
"Let’s go to bed, darling, and finish this. I am very horny and I want your cock in me. Come on, let’s go!"
Lisa was super horny, and so was I. She laid me on my back and started to caress me with the panties she had just taken off. I was so hard and excited I moaned.
Lisa said "Oh my. You love my panties, don’t you baby?"
"Oh fuck Lisa, I am so close."
"Wait now baby, don’t you dare cum yet! Let’s chat and play for a while. I want to enjoy these new feelings and openness, now that we both know you are a lingerie sissy girl!"
Lisa's head came to my cock and she kissed it, caressed it and rubbed it with her panties. She surprised me when she slipped the panties up my legs and pulled them on me, saying "Now that feels good babe, doesn’t it? So you are my little sissy now. Not a sissy cuckold. Just my sissy."
"Oh fuck Lisa, yes they feel lovely I must admit."
"Yes darling, you have played with them often enough to know, and I knew also!" She giggled. "So now you are coming out of the closet!" She rose up, kissing me as she took my hand and placed it over my silky covered cock. "Now babe, let me see you masturbate for me. Come on babe, don’t be embarrassed. You have done it often enough.
"I was so excited to be actually masturbating in front of Lisa, I knew I would not last long. Lisa knew it too. She stopped kissing me and said "Slowly now babe, make it last. Good. I love you in panties babe. I am going to get you your own. All men should wear silky sexy panties. I am going to make your own drawer full of lingerie for your own use. Darling, you got so excited reading about cuckolds and hotwives! I think you like the stories. You will have to read them more often, darling. I know I am. They are so exciting. I'm so glad Troy mentioned it. It’s quite common. I looked up husbands wearing lingerie and I was amazed that so many married men do. Some crossdress all the time.
"Just think darling... you letting me go out for a dinner with Troy. That would be mad!" She laughed like she had just told a funny joke. "You at home dressed in my panties and nightie, in my suspenders and stockings masturbating. It would be so exciting for the two of us! That sounds mad but so exciting! Ha ha!"
That was the trigger. I shot a load of cum in the panties as I pulled on my satin-wrapped cock. "Oh Fuckkkkkkkkk Lisa! Yes yes yes! Oh Fuckkkkkkkkk, yes yes yes oh oh oh god!"
"That’s it good girl, pull your cock. Keep cumming my baby, cum for me!"
As I slowed down, she kissed me hard then said "Oh baby, you are my little sissy. My lovely sissy. That was a huge cum, baby! You definitely need satin underwear like a sissy. The thought of me going out with Troy made you cum so hard. Admit it babe!"
"Well... Yes Lisa, for that moment when you said it, yes it did. The thought, not the fact Lisa... but he would love to take you out! Oh fuck!" The last little spasm of an orgasm hit me as I admitted it.
She said, "I know darling. I said it just to make you cum like the stories in the cuckold section on the internet. I really think reading those stories will enhance our sex life darling, especially now that we know you are a real sissy. Troy really does want to take me out as a work mate. Guess what, John?"
"What Lisa?"
"Tomorrow night you are getting into bed in panties and a nightie. We will not have any discussion about it."
"Really Lisa? Ok."
"Good girl. And tomorrow you are wearing sexy satin panties to work. I want you to feel sexy all day, baby. No more silly boxers for my girlfriend. I have always wanted you in panties, you have such a lovely girly bubble ass!"
The next day I had dinner ready for Lisa. I had a slight excitement as I remembered that Lisa was going to go to bed with me dressed in panties and nightie. I was excited all day long. Over dinner I asked Lisa how things went at work.
"Well now, John, I think you mean did Troy say anything. Yes he did. He asked me if my husband got angry when I told him about being asked out on a dinner date. I told him a little white lie. I told him you said thanks for being so complementary to his wife. He apologized again for the mistake but said the offer was still open if you would ever allow it."
"Lisa, what did you say?"
"I told him I didn't think you would allow it, but I promised to ask again. He said to tell you it would just be for the pleasure of my company and if you want to come as well, you would be most welcome. I told him that you wouldn't want to go. He requested that I at least ask you again if you would let your loving wife go to dinner with another man in a nice restaurant. And straight home again, of course!"
"Lisa he is very cheeky! He doesn't give up, and I didn't hear you saying no. You only said that I wouldn't approve. You didn't turn him down."
"Well John I did not mean it like that, but you'll never guess where he wants to take me. The Le Grande Paris!"
"Lisa, its impossible to get a booking there, and it’s so expensive! How could he afford that place? It’s the best restaurant in town!"
"I know John, and I would have nothing nice to wear to a classy place like that. You would have to buy me a new dress. If you approved for me to go, that is. He said he has a table for two booked for next Friday night and he needs someone to go with him.
"Oh John, I see you have a nice inviting bulge again! Are you as excited as I am darling? My pussy is wet from all this talk!"
Lisa knelt in front of John and opened his pants before he had a chance to say no. She pulled his hard cock from his silky panties and sank her mouth over it. She took it deep as possible, knowing she wouldn't gag as it wasn't big enough to choke her.
"Oh god Lisa! Fuckkkkkk, so good baby! What’s happening to us? Oh fuck Lisa, yes yes!"
John exploded straight into her stomach. Lisa swallowed it all and then quickly cleaned his cock before he got sensitive, then she put him back in his pants.
"Fuck Lisa, thank you for dessert! Oh baby anything for you. I love you so much!"
Lisa said "You will repay me later in bed, in your beautiful nightie and panties and lingerie I bought you. John, darling, you were so excited! I think the thought of approving me to go out - just for dinner - with Troy has you very excited! Let’s watch some TV, and then we will go to bed and play dress up, girlfriend!"
"Lisa, I'm going to read some stuff online instead."
"Good idea dear. Read the cuckold stories, but no wanking babe. That’s for later. Read more about the sissy cuckolds darling, it’s more like you yourself are. Just remember you love dressing up in lingerie and you're very feminine!"
- Next: Ch. 02
