Controlling Sissy Janice Pt. 01


I was uncertain which category I should post this story under. I love the crossdressing stories most, and this would certainly fit there. But the main action really is about cuckolding, so I’ve put it in the Fetish section.


I had thought that my wife was unaware of my crossdressing. Not only was I wrong but, as it turns out, I was the one unaware – -of the man she was having sex with at work. This is the story of how the truth came out and what happened afterward.

My wife Lilly works at a very high-powered law firm as an office manager. Though she’s not an attorney she works long hours. I’ve been a 9-5 office worker, managing accounts receivables for an insurance company.

In the period between when I got home and when Lilly got home I would dress in her clothes while I prepared dinner. I loved the bras and panties, the pantyhose and heels, and of course the beautiful dresses.

Since Lilly always called when she was leaving the office, so I could time dinner, I had time to change back into my male clothes before she got home, and place her clothes back in place (though I tried as much as I could to take them from the dirty clothes hamper so I didn’t need to worry how they’d been arranged. And I have to admit the smell of the used underwear and pantyhose was an extra turn-on).

On the eventful night I wasn’t expecting Lilly back until very late, as she’d told me there was a party at the office. I was in a pink bra and panty set, a black slip, white pantyhose, and a maroon bridesmaid gown Lilly had worn the prior year at a friend’s wedding. On my feet were a pair of white stripper heels, high platformed with long thick heels. Because my feet were bigger than Lilly’s shoes were the one of two things I had to buy for myself. On my head was the other personal item, a long brown wig that fell down below my shoulders. I didn’t wear makeup, as I was afraid of getting caught.

At 7:00, hours before I expected her home, Lilly walked through the door. I froze – what could I say or do? But Lilly didn’t seem shocked.

“Ah, so I finally get to meet the real you, James. I’ve been looking forward to this for a month now.”

“You knew?”

“Not until last month – and even then I just began to suspect. But once I became suspicious it was easy enough to find the evidence.”

“What tipped you off?”

“Actually, it was that dress you’re wearing now. I was casino oyna looking in my closet and when I moved that dress I noticed a smell. That dress smelled like the salmon almandine you’d made that night. It seemed to me there was only one way that could happen – if you had been wearing it while you cooked. Then I looked in the hamper and saw my bra, panties and pantyhose were on top. They should have been further down. I looked for further evidence, and that led me to the spare room. I found your box with the wig and heels on the shelf in the closet. And after that it was a simple matter of taking a picture of my closet each morning, and each evening I could tell which of my dresses had been moved.”

“Why didn’t you say something then?”

“I really didn’t know what to say. I was very annoyed that you’d hide this from me. But I can’t say I was surprised. You’ve always had a feminine aspect to you. You’re the only husband I know that enjoys clothes shopping with his wife. And you always had good suggestions as to what looked good. And when we made love you’re more like my lesbian lover. Yes, we have intercourse, but even then you’re slow and gentle. You’ve never pounded my pussy hard like a real man would.”

“But, honey, I am a real man! The fact that I’m respectful and gentle doesn’t mean I’m not.”

“Maybe, but the fact that you’re standing here dressed like a woman certainly means you’re not. I mean, I don’t even think of you as James anymore. In my mind you’re Janice now.”

I blushed and looked down at the floor. “So where do we go from here? Do you want a divorce?”

Lilly laughed. “No, I don’t want a divorce, but after what I have to say you might.”

I looked up, very, very worried, wondering what she could possibly say that would lead me to want to divorce the woman I loved so much.

“Once my view of you changed, Janice, I realized I could no longer view you as my manly husband. Oh, I’ve continued to have sex with you to keep up the façade until I knew what I would do. The answer actually occurred to me last week.”

“I was working late when I called Leonard into my office. I’m sure you remember Leonard, you met him at the firm Christmas party.”

I certainly remembered Leonard. Tall, muscular, suave, very handsome. A few years younger than us. And I definitely remembered him kissing Lilly under the mistletoe. It was a bit more than a simple slot oyna Christmas kiss.

Lily smiled. “At the time I thought you were jealous he was kissing me, but that’s what a real man would do. Now I think you were envious that it was me he was kissing and not you.”

I shook my head. “No, Lilly, I only like to dress as a woman, I don’t think about men in that way.”

“Dear Janice, if you’re going to lie it doesn’t help your cause when your dress gives you away.” She pointed at the growing erection pushing out against the dress.

“But, Lilly, I’ve never been with a man. In fact, you’re the only person I’ve ever had sex with.”

“Oh, I know you’d never cheat on me, Janice. Until last week I could have said the same thing about myself.”

I looked at her in shock. “You mean you had sex with Leonard?”

“Yes, as I started saying. I asked Leonard to come to my office under the pretext of discussing sensitive personnel information so I could ask him to close the door. It was at that moment I put my plan into action. I asked him if I could talk to him about a personal problem.

“I told him that I was convinced my husband was a sissy who dressed up like a woman, and that I no longer felt like he could be the man in my life.”

“Lilly, you told Leonard? Why would you do that? How can I ever face him again?”

“Well, I had to tell someone. Unlike you I didn’t want to keep this a secret. And I told Leonard because I knew what he would do next. He locked my office door and then came up to me, pulled me to my feet and wrapped me in his arms. He kissed me deeply and started massaging my ass. I moved my hand to his crotch. Not only was he hard, he was huge! So much bigger than you are, Janice!””

I felt humiliated by her story and her comments. Unfortunately, my cock betrayed my true feelings, as it was now very hard. Lilly noticed, pointed at it and laughed.

“I’m glad this is turning you on, sissy Janice. Wait until you hear the rest. I went over to my office couch and bent over. Leonard came up behind me and pulled my dress up. Luckily, I’d had the foresight to remove my panties earlier, or else they’d have been soaked. I pushed my ass up to him, and he knew just what to do. He jammed that huge cock right into my pussy. No slow entry, no gentle movements. He just jammed it in all the way and held it there. I came right away! Do you know I’ve never cum canlı casino siteleri from your cock, Janice?”

I was now thoroughly ashamed. It was clear that I’d failed Lilly as a real man. Not only was my cock not enough for her, here I was dressed in her lingerie and a bridesmaid dress. Of course, to make matters worse, my little cock was straining against the dress as she told me about her being pounded by Leonard.

Lilly reached over and took my cock in her hand through the dress. “Oh, Janice! He fucked me and fucked me! It was a good 20 minutes of just in and out, in and out.” Lilly was breathing hard now, and started to slowly stroke my cock. “I have no idea how many orgasms I had, but I do know the biggest was when he slammed into me one more time and filled me with cum! I have never had an orgasm like that!

I was breathing faster and faster. “When was this Lilly?” I asked.

“Last Tuesdsay.”

My mind thought back to that night. “But that night we…”

“Yes, we had sex. But remember I didn’t want you to put your cock in me? How I just had you go down on me? Yes, Janice, that night was the first time you tasted Leonard’s cum. But it won’t be the last.”

“You asked me how you’ll ever face Leonard again? Well, my dear Janice, you will face him dressed like the sissy you are. And you will do whatever he or I tell you to do.”

That was all I could take. Between Lilly’s story and her stroking I exploded with an orgasm, flooding the dress with my sperm. And Lilly shuddered, clearly having her own orgasm as I had mine.

As we both came down from the heights, Lilly kissed me. I asked her whether the story about the party at the office was a ruse. She said it was, as she wanted to catch me so that there could be no denial.

“So, where do we go from here, Lilly?”

“First we go upstairs. I want you to strip naked, then you are going to take a shower with hair remover. You look nice in this dress dear, but I want you hairless so you look nice in lingerie or swimsuits.”

“So you want me more passable?”

“Not entirely, Janice. I want you to look more feminine, but I want to keep you looking like a man in woman’s clothing – a sissy. You will start growing your hair long so we can style it, and your eyebrows need to be shaped. And of course we need to have your ears pierced.”

“But how will I go to work like that?”

“Well, Janice, you have three choices. You can have them realize that you’re a sissy fag. You can tell them you’re officially transitioning. Or you can quit and find another job that will only know you as Janice – because that is your only name from now on.”

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