You know, this is the fourth time this week I’ve seen you looking at crossdressing porn on Reddit. I think we need to talk about this before I write you up for creating a hostile workplace environment.
Oh, you didn’t think anyone could see you? Didn’t you notice this little gap between the cubicles? Stop waffling and get in my office. Now!
Come on, sit down. Relax. And look at me when I’m talking to you! Why do you think it’s OK to be looking at that stuff?
No, I don’t mean why do you think it’s OK at work (laughs). I mean, why do you like it? Do you get off pictures like that?
You don’t dress like that? Sure you don’t…. OK, maybe not, but I can tell you think about it.
Well, I think it’s time for you to start.
What do I mean? I mean, I think you need to come with me tonight and you can find out what it’s like. I’m leaving in 10 minutes. Be back here then and you can follow my car.
Don’t be nervous, nobody will care that we’re leaving together.
I hope you had an easy trip. Here we are. And here’s my wife. Meet Susan.
Yes, she’s hot. Of course I can see you looking at her nipples. Do they turn you on?
I knew they would. Tell her!
You don’t have to be so awkward about it! I’ve already explained to her that you’re here to learn about crossdressing. I’ll help you with clothes and she’ll do your makeup.
Oh, yes, makeup. I think you’ll make a lovely gurl.
Here, have a few tokes on this pen. It will help relax you.
I’ve put some clothes out for you on the bed in the playroom here. Come on in, hurry up, what do you think?
I know you’ve never worn anything like that before. That’s the point, right? I can tell it turns you on, I can see that nice bulge in your pants.
No, I’m not gay, I’m bi. And Susan and I are very open-minded. Now, take your clothes off. Would you like her to help you?
Well, I can see you liked that! You have a nice body. You look pretty hot with your cock leaking in your underwear, but I think I’d better pull them off now, too.
Well, isn’t that nice. Feels so warm in my hand. Do you like when I tickle your cockhead?
I thought so. OK now, put these stockings on and then I’ll help you with the garter belt.
Have some more. I get really horny when I’m high, too.
Oh, I can tell this is really turning you on, so I have a special treat for you. Close your eyes.
I know that felt a little weird with us making adjustments, but look at you! Now you’ve got breasts all of your own. That’s seven pounds of silicone wrapped around your chest. Don’t they feel good when you bounce them around?
Of course it’s OK to touch them. Feel those hard nipples! They look like it’s always wintertime, haha.
So put on the panties now. No, not like that, push your cock over to one wide so it’s inside them. Barely. I like that.
And now you can put on the dress. With that breastplate, you never need a bra!
Here’s a choker to wear, it’ll cover where the silicone meets your neck. And some bracelets. And earrings, oh, we’ll have to get you pierced for next time, I think.
You look really nice. No, no mirrors yet, not until Susan does your makeup. She’ll start with some concealer to cover up your stubble, but fortunately it’s pretty light already. Otherwise we’d have to shave you.
Yes, all over your body, but we’ll save that for next time,
Yes, I think the purple eyeshadow will be nice. Matches yours, dear. And that’s a great choice of lipstick. Make sure the wig stays in place.
Well, now it’s time for you to see. Close your eyes and I’ll guide you over to the mirror. Oooh, I love how your cock feels under that tight dress.
Here we are! What do you think?
I think so, too, and so does Susan. You look delicious!
I’m going to change clothes while you chat with Susan, see you in a few minutes. I hope you’re enjoying having us stroke your cock!
What are we going to do now? We have a dinner date, my pretty little friend. Do these shoes fit you? Oh good. I hope the heels aren’t too hard. You’ve never worn heels before, have you?
Your sister’s? Oh, that’s hot! I’m glad these are comfortable. You seem fine walking in them.
Now let’s go out to the car and take the next step in this adventure.
Source: reddit.com/r/sexystories/comments/jsfd47/forced_to_crossdress_half_a_dialogue_part_1_oc