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No, you won’t, little man, you’ll wait right here.

I don’t know how long I’ll be, but that’s no concern of yours. You’re to wait here, like a good, obedient little puppy, and hold my purse while you wait for me, your master, to return after she visits her new friend. Now, if you don’t think you can do that, I’ll be happy to put your collar on and leash you up. Will that be necessary?

You like my sweater, do you? Well, thanks, but, it’s a little small on me… you want it? I think it’d fit you better…

No silly, I won’t date you, but, I will let you be my slave. That’s what you really want, isn’t it?

She looked at me for a moment, thinking, no doubt pondering whether or not I was being honest and sincere or sarcastic and disingenuous.

I had just said “have a good night”, but she knew that I knew she had a date, and she also knew I had a massive crush on her after my pathetic, tear-filled confession the day prior.

Finally she asked “do you mean that? Really? ‘Cause it would mean so much to me if you do… it would mean we’re truly still friends, and you know how important that is to me…”

“Yes, I mean it,” I answered, “it really hurts, I still have feelings for you, and I think I always will, but our friendship is important to me too… more important than my own selfish feelings…”, then I added, “you look so beautiful, and your date is so tall and hot AF, so please go and have a good time.”

“You’re such a good friend…” she said with a smile, “please stay here tonight so I can tell you all about it when I get home, okay?”

“Sure, I can do that,” I answered, “I’ll just do the usual, get your laundry done and clean the bathrooms, and then I’ll sleep on the couch-“

“Thanks buddy,” she replied, “and hey, if you wanna wear one of my nighties or baby doll dresses to sleep in, feel free to- ‘kay, byeee!”

Well? What do you think sissy? You’re wearing the pink dress- that’s already been decided- but I’ll let you choose which sweater to wear with it tonight- they’re all so feminine and heavenly to the touch that your “special man” will have his hands all over you!

What? Aren’t you excited for your first date with a man?

Oh… hehe, it’s okay to be nervous… a man’s attention, especially when he’s so big and tall, can be a little intimidating, and a sissy like you will naturally be a bit flustered, but all you gotta do is follow his lead, do as he says, and try to relax and enjoy it…

Now, which sweater will you choose?

Look, I don’t mean to be mean, but you’ve got to know by this point in your life that you’re not really seem as a man, right? A short, nerdy, wimpy little guy like you just isn’t the manly type, and like, come on, seriously, I’m not saying anything you don’t already know, am I?

Have you tried feminizing? I bet you have, haven’t you? Trying on panties, dresses, skirts, blouses, girly things? Maybe a soft fuzzy sweater like mine? Aww, you’re blushing… you don’t need to be ashamed of it you know- I mean, a real man would be ashamed, but for a sissy like you, it’s just part of figuring out who you really are…

They just smiled, seemingly on the verge of breaking into laughter as I stood there, wearing the skirt and fuzzy sweater they instructed me to put on. Too afraid to complain and certainly too meek to argue, I just went along, confirming what a sissy I am. I blushed with shame so severe, I was nearly to the point of tears.

Then, my wife’s friend said “see? I told you he’s not really even a man… that’s why it’s not really cheating…”

“You’re such a good friend,” my wife replied, her smile just beaming, “now I can go on our double date tonight and not feel the slightest bit guilty…”

“And you- Sissy- what do you have to say about it?” her friend demanded.

“I don’t know,” I answered quietly, nearly a whisper, and wanting to get the whole humiliating thing over with, said what I thought they wanted to hear. “uhh… you’re right, I guess… you should go out with your dates and have a good time tonight?”

Their smiles disappeared and a stern, cross look beared down on me from them as they both crossed their arms. My wife asked “is that a question? Or do you really want me to have a good time when I go out with a real man tonight and leave you home to do housework?”

I course corrected quickly “I’m sorry… please, yes, please have a good time tonight with your date. You deserve to be with a real man, and I deserve to stay home and attend to my chores.”

“Better.” my wife responded.

Yes, I do… I do think you’re a complete sissy, and in fact, I will have you wearing my soft, feminine clothing before you can even say “yes ma’am”.