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A Husband Named Cathy

Story Info
A husband's dream comes true. He becomes Cathy.
2.3k words
4.4
146.7k
120

Part 1 of the 3 part series

Updated 04/27/2023
Created 03/06/2017
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When my wife Jane first found out about my naughty little secret she flew into a rage and launched into a tirade calling me a lying, duplicitous, deviant, degenerate pervert sissy faggot. She stormed out of the house slamming the door behind her.

About an hour later she returned and had calmed down. In a very apologetic tone she said that she was sorry and told me that if dressing up like a girl gave me pleasure she would be okay with it as long as I wasn't a homosexual. She would keep it our little secret and never tell anyone that I was a girlyboy.

I was shocked at the turnaround. She said she understood my fantasy and that she would help me become the girl of my dreams. She said I needed guidance on grooming, fashion, and style and that she wouldn't allow me to dress like a cheap floozy but would make sure I was always elegant and ladylike. I couldn't believe my ears. This was a dream come true. I was in sissy heaven.

The next day was a Saturday and she bought me my first bra, a fantastic pair of ultrasheer pantyhose and a pair of spike heeled pumpsI put them on and she told me how pretty I looked. That day she plucked my eyebrows and removed with some cream the sparse hairs on my chest, underarms, and genital area. I felt so naked and smooth all over and couldn't believe how wonderful it felt wearing nylons without hair on my legs.

Jane said that she was having fun playing dress-up with me and that she hadn't had this much fun since she was a young girl playing with her Barbie doll. She said that this was even better because I was her Barbie and I was real and could talk and react. She admitted that the scene excited her and was getting her aroused.

She called me "princess" and "kitten" and lovingly referred to me as "my little sissy," and remarked on how my "clitty" would get so hard in my pretty pink panties. She taught me all about makeup and pretty soon I could apply it myself. I would get so aroused when we both stood in front of the mirror putting on our mascara in the mornings. One day she brought home an array of nail polish and matching lipsticks and told me it would please her if I changed my nail color every day for her. I was thrilled. Jane said that a beautiful babe like me should have girl name and that's when she began calling me Cathy.

In the next few weeks I went shopping with her always wearing a bra and pantyhose under my male clothes. We would pretend the clothes were for her but she always asked me my opinion when buying things. Then we would return home and I would model the new clothes in a private fashion show for her. I had many outfits. One day I would be Business Woman Barbie and the next day Disco Barbie. Then, Secretary Barbie, Airline hostess Barbie, French maid Barbie etc... She was turned on by the experience and I was perpetually erect. She told me that although I wasn't a real female that I was girlier than most girls.

Although she showed decreasing desire to have normal sex with me she still always brought me to orgasm by mouth or by hand while talking sexy to me, remarking with things like, "O my sissy is aroused. She's coming in her pantyhose. What a naughty bitch you are!" I was loving every minute of it.

After about 2 months she told me how proud she was of me. She said I looked passable and could go anywhere as a girl without being noticed. To prove it we went out dressed casually one day. I was wearing tight jeans and a sheer top over my black bra and some light makeup and flat shoes. She took me to get my ears pierced and bought me a few pair of dangly earrings. I felt so girly wearing them. Then we went to a shoe store and bought stiletto heels together. Jane told me that I walked so naturally in heels that one would think I had been wearing high heels my whole life. Nobody in the street knew that I was a sissy. I looked like any average girl going shopping

.

It was the third month when everything changed.

One day Jane came home from work and told me we needed to have a talk. She was quite serious. She began,

"You know, Cathy, remember when I told you that I loved playing Barbie with you? Well, real girls, at a certain point, get tired and bored playing with Barbie. This usually occurs when they start getting interested in boys and in having sex. I'm afraid that has happened to me again. You see, Cathy, I have been cheating on you with other men. On Saturdays when I go to visit my sister and sleep-over at her house in the suburbs we go out clubbing to pick up men and bring them home for a one-night stand. Also, you know my friend Toni with whom I go to the gym every Tuesday and Thursday evenings? She's bisexual and I have been having a lesbian relationship with her. We also sometimes go out to pick up men and get laid at her house."

I was shocked at these revelations but really couldn't complain or blame her, given the circumstances of my own little hobby. I said that I didn't mind her adventures and that she really didn't have to tell me about them since I had been none the wiser.

That's when the bombshell hit. Jane said,

"I think you should move out."

I was dumbfounded.

"Why?" I whimpered.

She said I was cramping her style and that she was tired of sneaking around having sex in other peoples' homes and could never bring a partner home because I was always around and she had to keep me a secret.

"It would be different if you were a social sissy but you're not. You're a secret sissy and you cramp my style. Toni wants to move in with me and with you here she can't." She said

That's when I offered to be her social sissy. I would agree to have Toni move in and naturally, she would learn my secret. Jane said we could give it a try but no guarantee that it would work out. I agreed to try my best to accommodate them.

Toni moved in the next day. Jane told me to paint my nails crimson red and to wear the new little black dress and open-toed pumps that evening. Toni was a very attractive short-haired lesbian type with a punk hairdo. She was obviously the dominant one of the relationship with my wife Jane. She also talked and acted kinky in contrast to my demure wife. Toni looked at me and said,

"O what a precious little girly-boy you have here, Jane! I never knew you married a faggot."

When I protested and replied that I wasn't gay Toni interrupted,

"Oh, come on Cathy. I have known many gays and can spot one a mile away, and if you're not gay I'm the King of England!"

Toni asked Jane if I was an obedient sissy and Jane said that I was very compliant with her wishes at all times.

"If she's such a good sissy do you think she would show me how she masturbates?" asked Toni.

Jane, very proud, said to me,

"Cathy, why don't you show Toni how you jerk off in your pantyhose?"

I was excited with all this talk and hiked up my dress and began fondling my clitty in front of the two women while Toni commented,

"How cute! I love watching sissies get hot. It's so sexy. Come for me, Cathy. Come in your pantyhose for the girls."

I exploded with a stream of cum squirting into my nylons in front of the two women.

"What a naughty little bitch! Cathy you're such a slut." Toni commented.

The women laughed as I hastened to clean up the mess I just made and went running out of the room to remove my pantyhose as they laughed heartily.

We got into a routine. Toni and Jane now had the master bedroom and redecorated the guest room in pink for me. Sometimes they would have hot lesbian sex in front of me and made me watch while I masturbated. Since I was unemployed, the housework became my responsibility as welll as personal services. They had me paint their toenails and sometimes cum on their toes and lick up the come while they taunted me. Toni was constantly teasing me with comments like,

"Cathy, you should really learn to suck cock. I think you would love it. Those pouty lips look so inviting to guys. They would love shoving their cocks into your pretty mouth."

Jane usually said something like,

"C'mon Toni, leave Cathy alone."

One day Jane had to go out of town for 3 days to attend a funeral of a family member in California and she told me that she would be leaving me home with Toni for a few days. While she was away I was to obey Toni just as I obeyed Jane. I was apprehensive about being left alone with Toni since she was so kinky and unpredictable.

The first day alone with Toni was memorable. I was wearing a clingy shift, sheer pantyhose and heels, and was fully made up when the doorbell rang. Toni opened it and it was a guy.

She smiled and said,

"Cathy, come here. I want to introduce you to Jack. Jack, this is my sissy roommate Cathy."

I smiled at Jack and was blushing as I faced the first man who had ever seen me dressed as a woman. Toni continued,

"Cathy, I asked Jack to come over because I think it's time for you to learn how to suck cock. I'm certain that it's an experience you will love."

As I stood there trembling Toni opened Jack's pants and took them off. She told me to kneel on the floor and Jack approached me waving his semi-soft dick in my direction. Toni said that Jack had a real man's cock and would like me to kiss it. She held his cock near my face and told me,

"Kiss it. Kiss it right now."

I did.

Then she told me to lick it with my tongue which I also did. Just then, Jack grabbed my head and shoved his hard cock into my mouth. Toni told me to suck it and to swirl my tongue around it while I sucked. I couldn't believe what I was doing! Toni provided commentary

"Cathy looks so pretty with a cock in her mouth. She has always wanted to do this. Cathy, you're sucking a man's cock just like a real girl. Pretty soon Jack will be cumming and you need to make sure you swallow it all."

Jack then exploded in my mouth and I couldn't swallow it fast enough and he wound up cumming all over my face. Toni laughed,

"Oh Cathy, you need to practice your swallowing or else you'll always be repairing you make-up. Look at yourself. You have cum all over your cheeks and it's dripping down your chin. You look like a real cum slut, now. "

She went on,

"Cathy, congratulations. You just sucked a man's cock. You're now officially a cocksucker. Jane will be so proud. From now on when I ask you what you are I want you to reply, 'I am a cocksucker.' Do you understand?"

She then asked me what I was and I answered,

"I am a cocksucker, Toni."

Jack chimed in,

"...and a really hot little cocksucker she is."

I was humiliated...but very aroused at what just occurred.

Jack left , squeezing my ass cheek as he departed.

Toni was a woman just full of surprises. The next day she went out early and came back with a shopping bag and announced,

"Cathy I was so proud of you yesterday and the way you behaved with Jack. Now that you are a cocksucker, I have a few things to help us celebrate your new status. It's time for you to wear big girl nylons. No more pantyhose for you. Look at the pretty black satin garter belt I bought you. It goes with these very sheer seamless stockings with reinforced heels and toes. I also bought you a pink butt plug. When I insert it you will have a much more feminine stride when you walk. You are going to love it."

She continued,

"I am going to teach you some basic flirting techniques. Put on the nylons and garter belt and your black pumps. Cross your legs. Now bend you ankle up. The heel of your pump just popped revealing the reinforced heel of your stocking. Observant men will notice the reinforced heel and conclude that you wear stockings rather than pantyhose and this will get them excited. When you catch them looking, just dangle your pump on the toe of your foot. This lets them know that you are looking at them too."

"That's it. Great. You pop your pumps like a real flirt! Nice dangle, girl. Come here and I will lube you up for your butt plug." With that, she inserted the butt plug in my "tranny pussy." I felt strange but it wasn't unpleasant at all. Toni patted my ass and said, "You're a sexy little vixen, Cathy. I'm sure we are going to have lots of fun before Jane returns home."

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Riki1942Riki1942over 1 year ago

I'm single so I can do my hair in a feminine style, wear makeup and fully dress anytime and for as long as I want and, although I currently have a steady boyfriend and am only having sex with him, I think of myself as a Sissy Slut.

I have never done it but, the thought of a woman watching and talking to us while I have sex with my boyfriend really turns me on.

It's strange because I don't feel like I'm an exhibitionists. Other gay guys have seen me having sex, like in a threesome or something, but that was hot because of the fun and not so much that a guy was watching me.

It would have anything to do with being dominated because she was telling me what she wanted me to do, because I would happily do what she wanted to see, and I DEFINITELY wouldn't feel humiliated! I think it would make me feel proud to have her see what a good sissy that I can be.

There is just something special, not to mention kinky, about the thought of a her, (being a woman) seeing me in my makeup, all dressed up like her and doing the things with a man that she would do.

Riki

cdCindy1cdCindy1almost 2 years ago

It really hit home with me when Toni told Cathy that he/she was gay. I too am a sissy husband who has finally admitted to myself that -- yes -- I AM GAY. I love men, even though I'm still married to a woman. I truly wish she would cuckold me, with a man or a woman (or both) whatever she wants.

Claudia69Claudia69over 2 years ago
Cute Story!!

I love stories where the wife's girlfriends help train the Sissy....

IntercontinentalIntercontinentalover 2 years ago
Compelling

A good story that pushes all the right buttons.

No girl forgets the first time she has had a cock in her mouth.

Brendalee43Brendalee43over 3 years ago

Pantyhose! The gateway clothing to sluttyville.

I'm just the voice of experience.

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