It's official: I am a sissy cuckold
Part 1 - I begin to have suspicions
Cassie and I are an average couple; middle-aged, middle of the road, leading a regular 9-5 kind of lifestyle.
Our sex-life was average. Once-a-week, usually on a Sunday morning. Missionary position, lasting about 10 minutes.
Cassie used to dress up for me, and I would often construct a fantasy scenario that we would act out .... but not now. That kind of thing is a thing of the past .... until now.
Now my life has been turned upside down and I still haven't worked out if it is a bad thing, or a good thing.
So, let me explain.
About 2 months ago I noticed that Cassie was buying a lot more sexy lingerie, tighter dresses, higher heels and spent a lot more time and money on her hair. It was like she was going back in time, and getting younger. She spent a lot more time going out "with the girls" and her work seemed to take up a lot more of her time. No more the 9-5 routine.
Apparently she had got a promotion and her boss was now a lot more demanding of her time. Thank goodness, I thought, we could really use the extra money and, believe me, Cassie was earning a lot more money. Her pay had more than doubled in the last two months.
But, (there is always a 'but'), Adam, Cassie's boss would often call her at odd hours. Often late at night, even though she had only just got back from work, or a work event where Adam would have seen her only an hour or two before. She would always go into another room to take his calls saying that she didn't want to disturb me.
I soon noticed that Cassie was now wearing all her sexy new clothes to work. Sometimes she would take spare clothes with her to work, telling me that she had to attend a 'work event', such as a cocktail party in the evening. I was beginning to get worried, but then I felt guilty because it meant that I was not trusting Cassie. I had to give my head a wobble, and tell myself that Cassie is doing her best to bring some more money in, and if that meant dressing up a bit to impress her boss, then so be it.
Maybe she was flirting with her boss, well so be it if that is all it takes to double your money. So, I calmed myself down with those thoughts ... but the nagging doubts kept returning. But then, and here is the strange thing, whenever those doubts crept back in I noticed that I was getting oddly excited too.
The first bit of hard evidence that I found was when I mistook Cassie's phone for mine. I picked it up by accident and I noticed that Adam, her boss, had sent some pictures. Opening up the pictures there were three 'dick pics'. Oh my goodness, Adam was huge! the message with the pictures said ... "This is what you are doing to me Cassie .... don't keep flirting with me Cassie .. I know you want *this* don't you". My head was swimming, I was astounded. But worse was to come. I scrolled up and I found some selfie pics that Cassie had taken in the full-length mirror in our bedroom. The pics were of Cassie dressed only in lingerie and heels. The caption that she wrote was "Hello Adam, I just wanted to say 'thank you' for the recent promotion and for the raise in salary ... this is what I have bought with my raise. I hope you approve!!"
I became instantly excited and erect. Omg, I cannot remember the last time I felt this aroused.
Cassie then walked into the room ... "what's up with you" she said, seeing my flustered state; I couldn't work out whether I was aroused or angry. So, I confronted her with the pictures.
Oh, my goodness! I have unleashed hell. Cassie went mad. I have never seen her so angry. She was angry that I had looked into her phone, but she was also angry that she felt that I was trying to control her. "It's only a bit of fun" she said, "I'm allowed to have fun" she continued, "I can do what I like ... especially as I am the one who is bringing in most of the money".
Her fierce reaction took me by surprise. I had stumbled in on Cassie's new world and there was no way she was going to leave it, just because I say so. She told me that I had to accept what she was doing .... or else I would have to leave. Take or leave it was the message.
She reinforced the message by stating, very explicitly, that she hadn't had sex with Adam but she did really enjoy exchanging pics and that they regularly had telephone sex. Apparently, Adam really got off on the fact that he was making Cassie cum (on our bed) when I was somewhere in the house. She told me straight that if I keep whinging and whining that she would have real sex with Adam.
I soon backed down under such withering fire from Cassie, and I apologised. Why was I apologising? I couldn't work it out, but I just felt that I had to back down, and be compliant with her wishes.
She smiled a triumphant smile, and then she added "Oh, and by the way, I am working late tonight ... with Adam .... I may be very late"
Part 2 - Cassie humiliates me
Sure enough, Cassie was late coming home that night. Naturally enough my mind was racing as to what Cassie was getting up to, with such thoughts as these racing through my mind:
https://xhamster.com/photos/gallery/13302312/352262749
My mind was racing, and my emotions were a strange cocktail of fear, anger and excitement. Fear and anger I can handle, but excitement? What was exciting me? Well I had seen what Cassie was wearing before She left for the office. I knew that if She was flirting with Adam tonight, then he would be feeling absolutely rampant, if this is what he gets to see:
https://xhamster.com/photos/gallery/13302312/356628447
I was so excited thinking about how aroused Adam would be if Cassie was flirting with him.
I stripped off, so I could masturbate. As I lay back on the bed caressing myself, I noticed that Cassie had left about three pairs of panties on the bed. I reached for a pair of silky black panties and pulled them on. Omg, I didn't think I could get harder or any more aroused, until I felt the caress of the silky panties on my cock. Oh, I was in ecstasy now. I was totally lost in the moment.
I was shaken out of my trance-like state when I heard a car pull up outside on the driveway. It was a Range Rover Velar with personalised number plate AD4 M1, or ADAM 1. I looked through a gap in the curtains for about 10 minutes, nothing seemed to be happening. There seemed to be some movement in the car but the windows were dark and it was difficult to clearly see.
Eventually the passenger door opened and Cassie gets out rather awkwardly, owing to the height of the car and the height of Her heels. Hey! did I see correctly? As Cassie descends from the car Her short skirt rides up to reveal her stockings tops, ... and nothing else .... She's not wearing panties! or was it a trick of the light.
The front door opens and I hear Cassie coming upstairs, and it is only then that I remember I am naked apart from Cassie's black panties covering my half erect cock. I quickly slip out of the black panties and throw them in the corner just before Cassie enters the bedroom and turns on the light. I stand, naked and rooted to the spot, in the middle of the room, my cock now semi-erect.
Cassie, taken by surprise, giggles at the sight of me. It's only then that I notice she is holding her panties in her hand. Before I have time to say anything, Cassie immediately takes the initiative. "Have you been wanking? She demands. "Here, have something that might help", and she throws her panties at me. "Go on, put them on ... I know you want to. They will make you feel good."
I had lots of reservations about this situation, but my urgent desires overcame them very quickly. I eagerly stepped into her lovely red satin panties and pulled them up over my swollen but semi-hard cock.
“Oh my my” Cassie said “you slipped into my panties like an expert. If I were a betting woman, I would say that you have played this game before”. I mumbled something incoherent in response, which Cassie took to be a ‘Yes’. My hardening cock told its own story. My cock was delighted to be in Cassie’s panties and was soon hardening.
“Go on darling, give me a show. Show me how you wank in my panties”, she giggled. She reminded me of Lady Sonia in one of the many ‘jerk-off instruction’ videos that I had watched.
I didn’t resist. I couldn’t resist if the truth be told. I lay back on our king-size bed and started to masturbate. The combination of Cassie’s panties and Cassie’s jerk-off instructions made me delirious with pleasure.
As I wanked, I saw Cassie taking photos of me. I didn’t care though. All that interested me was the intense pleasure that I was feeling. As she took the pictures she continued giving me instructions … “Go on, wank it for me darling …. show me how big you can get …. Don’t cum yet darling … hold your cum for me …. You will have to beg me to cum …. “
Lost in my pleasure, I only vaguely noticed that Cassie seemed to be texting. Omg! She is sending the photos to someone. Oh no, surely she is not sending them to Adam. At that moment she puts the phone to her ear, then says “Hi darling, yes, did you get them? Yes? What do you think? Awesome aren’t they!”
I couldn’t hear clearly what Adam was saying, but I could certainly make out a lot of laughter coming from him. Cassie was giggling too, and every so often she turned to me and said “go on, keep going, but don’t cum yet [giggles]”.
She hung up and turned to me and said what I desperately wanted to hear “If you beg me nicely, you can cum for me”. I did as I was told. I begged and begged. I pleaded in desperation. Finally Cassie told me to cum. With just two or three final strokes my cock exploded and I shot huge ropes of cum all over my stomach, chest and face. Omg, I don’t recall ever having an orgasm with such force and I had never shot my load so far that it reached my face. Cum pooled around my eyes and my lips. I licked my lips and tasted cum for the very first time. Cassie took a couple of photos of my face, and sent them to Adam.
I lay back on the bed. I was naked and embarrassed. Cassie’s panties, which were now down by my knees, I pulled up. I didn’t take them off. I was almost naked and covered in my own cum but, somehow, I felt a degree of comfort in pulling up the panties, as a way of covering my embarrassment.
I didn’t know it then, because I didn’t have the presence of mind, but with the benefit of hindsight now, I can see clearly that I had allowed Cassie to get me to the second part of my ‘journey’.
The first part of the journey was to accept that Cassie would flirt with another guy. In this second part I have allowed myself to be humiliated by my wife, in front of the guy who was almost certainly cuckolding me, although I still didn’t know for sure at this time.
How do I explain how I allowed myself to be so humiliated? I can only guess that the humiliation was all part of the excitement. This was pure excitement, the like of which I had never experienced before. Maybe I was getting hooked on the rush that the humiliation gave me.
Part 3 - Cassie Sissifies me
I woke to the sound of the shower from the bathroom. Cassie was already up and getting ready to go. She came back to the bedroom, towel wrapped around her, commanding me to get ready too. “C’mon, c’mon” she said, “we have a busy day ahead”.
I was confused. “What do you mean, ‘busy day’? I said.
“Never mind, just get showered, and I will tell you more in the car”.
I did as I was told, which seemed to be becoming the norm and, before I knew it, I was driving, somewhere with Cassie.
It turned out that Adam had given Cassie the day off, and he told her to take me shopping. Cassie explained that Adam, after seeing the pictures of me last night and what Cassie had told him about me, thought that I was merely ‘cosplaying’ when I dressed up in Cassie’s lingerie. Adam wanted me to become fully feminised. But, and this is the thing, he didn’t just want to feminise me, he wanted me to be a replica (as far as possible) of Cassie.
Omg, I thought, this guy Adam is on a full-throttle power trip. He was controlling my wife, and now he was controlling me … and I hadn’t even met him. But somehow, for some reason, I seemed so easily persuaded by Cassie. I went along with it all, because this is what she wanted, and I was desperate to please her.
To cut a long story short, we went to several department stores and specialist lingerie stores. Cassie didn’t disguise why we were there. In each store she came right out with it, “We want two of everything, a ‘his and hers’”. The women in the stores were very professional, and arranged for discreet fittings for me, but no matter how discreet they were, it didn’t diminish the humiliation I felt.
My humiliation didn’t end with the clothes shopping though. Next up was the beauty parlour. All over waxing and depilation was both time-consuming and humiliating for me. But I guess that was the point. Adam wanted me to be humiliated to the max.
Then came the pedicure, manicure, eyebrows, skin laser treatment, facials and makeup followed by the wig fitting, so that I had hair to match Cassie’s. It was a complete makeover.
The final stop was at a fetish store, where we bought shoes and some other ‘accessories’, such as a collar and lead and, worryingly, a cock-cage.
By this time, I was completely maxed-out on my two credit cards. I had spent a fortune, but Cassie seemed ecstatic. I don’t think I had ever seen her so excited, so for me it was all worth it. I just loved seeing her look so radiant.
It was early evening by the time we got home, and Cassie demanded that we both have a ‘trying on’ session. Cassie opened a bottle of bubbles whilst we tried on our new lingerie, hosiery, dresses, skirts, and shoes. Omg, I felt so good.
I hated to admit it by Adam was right, up until now I had only been cosplaying. But now, I really felt like a girl and, if the truth be known, I was feeling good about it. What made it especially good was that I knew Cassie was happy. She was very happy.
I didn’t know it then, but it wasn’t going to be long before I met the person who was making her happy .. Adam. This was not the end of my journey. Very soon I would be embarking on the next phase of my rapidly changing life.
Part 4 - Adam cuckolds me
Cassie and I are an average couple; middle-aged, middle of the road, leading a regular 9-5 kind of lifestyle.
Our sex-life was average. Once-a-week, usually on a Sunday morning. Missionary position, lasting about 10 minutes.
Cassie used to dress up for me, and I would often construct a fantasy scenario that we would act out .... but not now. That kind of thing is a thing of the past .... until now.
Now my life has been turned upside down and I still haven't worked out if it is a bad thing, or a good thing.
So, let me explain.
About 2 months ago I noticed that Cassie was buying a lot more sexy lingerie, tighter dresses, higher heels and spent a lot more time and money on her hair. It was like she was going back in time, and getting younger. She spent a lot more time going out "with the girls" and her work seemed to take up a lot more of her time. No more the 9-5 routine.
Apparently she had got a promotion and her boss was now a lot more demanding of her time. Thank goodness, I thought, we could really use the extra money and, believe me, Cassie was earning a lot more money. Her pay had more than doubled in the last two months.
But, (there is always a 'but'), Adam, Cassie's boss would often call her at odd hours. Often late at night, even though she had only just got back from work, or a work event where Adam would have seen her only an hour or two before. She would always go into another room to take his calls saying that she didn't want to disturb me.
I soon noticed that Cassie was now wearing all her sexy new clothes to work. Sometimes she would take spare clothes with her to work, telling me that she had to attend a 'work event', such as a cocktail party in the evening. I was beginning to get worried, but then I felt guilty because it meant that I was not trusting Cassie. I had to give my head a wobble, and tell myself that Cassie is doing her best to bring some more money in, and if that meant dressing up a bit to impress her boss, then so be it.
Maybe she was flirting with her boss, well so be it if that is all it takes to double your money. So, I calmed myself down with those thoughts ... but the nagging doubts kept returning. But then, and here is the strange thing, whenever those doubts crept back in I noticed that I was getting oddly excited too.
The first bit of hard evidence that I found was when I mistook Cassie's phone for mine. I picked it up by accident and I noticed that Adam, her boss, had sent some pictures. Opening up the pictures there were three 'dick pics'. Oh my goodness, Adam was huge! the message with the pictures said ... "This is what you are doing to me Cassie .... don't keep flirting with me Cassie .. I know you want *this* don't you". My head was swimming, I was astounded. But worse was to come. I scrolled up and I found some selfie pics that Cassie had taken in the full-length mirror in our bedroom. The pics were of Cassie dressed only in lingerie and heels. The caption that she wrote was "Hello Adam, I just wanted to say 'thank you' for the recent promotion and for the raise in salary ... this is what I have bought with my raise. I hope you approve!!"
I became instantly excited and erect. Omg, I cannot remember the last time I felt this aroused.
Cassie then walked into the room ... "what's up with you" she said, seeing my flustered state; I couldn't work out whether I was aroused or angry. So, I confronted her with the pictures.
Oh, my goodness! I have unleashed hell. Cassie went mad. I have never seen her so angry. She was angry that I had looked into her phone, but she was also angry that she felt that I was trying to control her. "It's only a bit of fun" she said, "I'm allowed to have fun" she continued, "I can do what I like ... especially as I am the one who is bringing in most of the money".
Her fierce reaction took me by surprise. I had stumbled in on Cassie's new world and there was no way she was going to leave it, just because I say so. She told me that I had to accept what she was doing .... or else I would have to leave. Take or leave it was the message.
She reinforced the message by stating, very explicitly, that she hadn't had sex with Adam but she did really enjoy exchanging pics and that they regularly had telephone sex. Apparently, Adam really got off on the fact that he was making Cassie cum (on our bed) when I was somewhere in the house. She told me straight that if I keep whinging and whining that she would have real sex with Adam.
I soon backed down under such withering fire from Cassie, and I apologised. Why was I apologising? I couldn't work it out, but I just felt that I had to back down, and be compliant with her wishes.
She smiled a triumphant smile, and then she added "Oh, and by the way, I am working late tonight ... with Adam .... I may be very late"
Part 2 - Cassie humiliates me
Sure enough, Cassie was late coming home that night. Naturally enough my mind was racing as to what Cassie was getting up to, with such thoughts as these racing through my mind:
https://xhamster.com/photos/gallery/13302312/352262749
My mind was racing, and my emotions were a strange cocktail of fear, anger and excitement. Fear and anger I can handle, but excitement? What was exciting me? Well I had seen what Cassie was wearing before She left for the office. I knew that if She was flirting with Adam tonight, then he would be feeling absolutely rampant, if this is what he gets to see:
https://xhamster.com/photos/gallery/13302312/356628447
I was so excited thinking about how aroused Adam would be if Cassie was flirting with him.
I stripped off, so I could masturbate. As I lay back on the bed caressing myself, I noticed that Cassie had left about three pairs of panties on the bed. I reached for a pair of silky black panties and pulled them on. Omg, I didn't think I could get harder or any more aroused, until I felt the caress of the silky panties on my cock. Oh, I was in ecstasy now. I was totally lost in the moment.
I was shaken out of my trance-like state when I heard a car pull up outside on the driveway. It was a Range Rover Velar with personalised number plate AD4 M1, or ADAM 1. I looked through a gap in the curtains for about 10 minutes, nothing seemed to be happening. There seemed to be some movement in the car but the windows were dark and it was difficult to clearly see.
Eventually the passenger door opened and Cassie gets out rather awkwardly, owing to the height of the car and the height of Her heels. Hey! did I see correctly? As Cassie descends from the car Her short skirt rides up to reveal her stockings tops, ... and nothing else .... She's not wearing panties! or was it a trick of the light.
The front door opens and I hear Cassie coming upstairs, and it is only then that I remember I am naked apart from Cassie's black panties covering my half erect cock. I quickly slip out of the black panties and throw them in the corner just before Cassie enters the bedroom and turns on the light. I stand, naked and rooted to the spot, in the middle of the room, my cock now semi-erect.
Cassie, taken by surprise, giggles at the sight of me. It's only then that I notice she is holding her panties in her hand. Before I have time to say anything, Cassie immediately takes the initiative. "Have you been wanking? She demands. "Here, have something that might help", and she throws her panties at me. "Go on, put them on ... I know you want to. They will make you feel good."
I had lots of reservations about this situation, but my urgent desires overcame them very quickly. I eagerly stepped into her lovely red satin panties and pulled them up over my swollen but semi-hard cock.
“Oh my my” Cassie said “you slipped into my panties like an expert. If I were a betting woman, I would say that you have played this game before”. I mumbled something incoherent in response, which Cassie took to be a ‘Yes’. My hardening cock told its own story. My cock was delighted to be in Cassie’s panties and was soon hardening.
“Go on darling, give me a show. Show me how you wank in my panties”, she giggled. She reminded me of Lady Sonia in one of the many ‘jerk-off instruction’ videos that I had watched.
I didn’t resist. I couldn’t resist if the truth be told. I lay back on our king-size bed and started to masturbate. The combination of Cassie’s panties and Cassie’s jerk-off instructions made me delirious with pleasure.
As I wanked, I saw Cassie taking photos of me. I didn’t care though. All that interested me was the intense pleasure that I was feeling. As she took the pictures she continued giving me instructions … “Go on, wank it for me darling …. show me how big you can get …. Don’t cum yet darling … hold your cum for me …. You will have to beg me to cum …. “
Lost in my pleasure, I only vaguely noticed that Cassie seemed to be texting. Omg! She is sending the photos to someone. Oh no, surely she is not sending them to Adam. At that moment she puts the phone to her ear, then says “Hi darling, yes, did you get them? Yes? What do you think? Awesome aren’t they!”
I couldn’t hear clearly what Adam was saying, but I could certainly make out a lot of laughter coming from him. Cassie was giggling too, and every so often she turned to me and said “go on, keep going, but don’t cum yet [giggles]”.
She hung up and turned to me and said what I desperately wanted to hear “If you beg me nicely, you can cum for me”. I did as I was told. I begged and begged. I pleaded in desperation. Finally Cassie told me to cum. With just two or three final strokes my cock exploded and I shot huge ropes of cum all over my stomach, chest and face. Omg, I don’t recall ever having an orgasm with such force and I had never shot my load so far that it reached my face. Cum pooled around my eyes and my lips. I licked my lips and tasted cum for the very first time. Cassie took a couple of photos of my face, and sent them to Adam.
I lay back on the bed. I was naked and embarrassed. Cassie’s panties, which were now down by my knees, I pulled up. I didn’t take them off. I was almost naked and covered in my own cum but, somehow, I felt a degree of comfort in pulling up the panties, as a way of covering my embarrassment.
I didn’t know it then, because I didn’t have the presence of mind, but with the benefit of hindsight now, I can see clearly that I had allowed Cassie to get me to the second part of my ‘journey’.
The first part of the journey was to accept that Cassie would flirt with another guy. In this second part I have allowed myself to be humiliated by my wife, in front of the guy who was almost certainly cuckolding me, although I still didn’t know for sure at this time.
How do I explain how I allowed myself to be so humiliated? I can only guess that the humiliation was all part of the excitement. This was pure excitement, the like of which I had never experienced before. Maybe I was getting hooked on the rush that the humiliation gave me.
Part 3 - Cassie Sissifies me
I woke to the sound of the shower from the bathroom. Cassie was already up and getting ready to go. She came back to the bedroom, towel wrapped around her, commanding me to get ready too. “C’mon, c’mon” she said, “we have a busy day ahead”.
I was confused. “What do you mean, ‘busy day’? I said.
“Never mind, just get showered, and I will tell you more in the car”.
I did as I was told, which seemed to be becoming the norm and, before I knew it, I was driving, somewhere with Cassie.
It turned out that Adam had given Cassie the day off, and he told her to take me shopping. Cassie explained that Adam, after seeing the pictures of me last night and what Cassie had told him about me, thought that I was merely ‘cosplaying’ when I dressed up in Cassie’s lingerie. Adam wanted me to become fully feminised. But, and this is the thing, he didn’t just want to feminise me, he wanted me to be a replica (as far as possible) of Cassie.
Omg, I thought, this guy Adam is on a full-throttle power trip. He was controlling my wife, and now he was controlling me … and I hadn’t even met him. But somehow, for some reason, I seemed so easily persuaded by Cassie. I went along with it all, because this is what she wanted, and I was desperate to please her.
To cut a long story short, we went to several department stores and specialist lingerie stores. Cassie didn’t disguise why we were there. In each store she came right out with it, “We want two of everything, a ‘his and hers’”. The women in the stores were very professional, and arranged for discreet fittings for me, but no matter how discreet they were, it didn’t diminish the humiliation I felt.
My humiliation didn’t end with the clothes shopping though. Next up was the beauty parlour. All over waxing and depilation was both time-consuming and humiliating for me. But I guess that was the point. Adam wanted me to be humiliated to the max.
Then came the pedicure, manicure, eyebrows, skin laser treatment, facials and makeup followed by the wig fitting, so that I had hair to match Cassie’s. It was a complete makeover.
The final stop was at a fetish store, where we bought shoes and some other ‘accessories’, such as a collar and lead and, worryingly, a cock-cage.
By this time, I was completely maxed-out on my two credit cards. I had spent a fortune, but Cassie seemed ecstatic. I don’t think I had ever seen her so excited, so for me it was all worth it. I just loved seeing her look so radiant.
It was early evening by the time we got home, and Cassie demanded that we both have a ‘trying on’ session. Cassie opened a bottle of bubbles whilst we tried on our new lingerie, hosiery, dresses, skirts, and shoes. Omg, I felt so good.
I hated to admit it by Adam was right, up until now I had only been cosplaying. But now, I really felt like a girl and, if the truth be known, I was feeling good about it. What made it especially good was that I knew Cassie was happy. She was very happy.
I didn’t know it then, but it wasn’t going to be long before I met the person who was making her happy .. Adam. This was not the end of my journey. Very soon I would be embarking on the next phase of my rapidly changing life.
Part 4 - Adam cuckolds me
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