In our time working together, you’ve never known me to have a girlfriend. We sit in a shared cubicle, and have been good work friends for about two years now. You’ve always felt comfortable talking about your relationships to me - even sex. Those conversations seem a little one sided, though - I always seem to clam up when it comes to intimacy.

It’s a Friday night, and we went out for a drink together. After a few, you ask me why I’m never dating anyone. I tell you that I’ve only ever been with one person, and it didn’t end well. I don’t want to talk about it, but you keep the drinks coming.

Finally I break down and tell you about my ex. She was a self described “size queen” and I was never able to satisfy her. She only wanted penetration, like a “real man,” but I could never make her cum that way. You’re the only person I’ve ever told this to, and we can’t help but feel close because of it.

We get a ride back to your place to have a few more drinks. Our conversation becomes more stilted & awkward the more we try to avoid talking about the closeness we feel. A few failed attempts a small talk later you throw caution to the wind and kiss me. Soon enough we’re tearing at each other’s clothes.

You pull my pants off and see it - a thin, 2.5 inch cock. Fully hard.

—————

This is where you come it. There are two paths that I see this scene going: humiliation, or encouragement. I’m open to the idea of this playing out with either a cis or trans woman.

Humiliation Ideas:

-You’ve never seen one so small. You can’t bring yourself to have sex, but maybe a handjob will do.

-You’re a trans woman with a huge cock - twice my size before you get hard. I cum so fast that it’s pathetic.

-You can’t wait to tell everyone back at the office about this.

Encouragement Ideas:

-You feel so bad that no one’s ever given me a real chance, and want to try everything with me.

-You’re a trans woman with a cock as small as mine (or smaller). You know how to have fun at that size.

-You’ve never made a guy cum as fast as I do, and it makes you feel sexy.

———————

I’m pretty chill - reach out if you’re interested. Cis and Trans women only, please. I don’t require you to write an essay for each message - just be collaborative.

Limits are scat, blood, etc. Other than that, be sure to let me know if you have any kinks that might play well into this scene!

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