1. Snowed In Roommates


    Date: 8/4/2024, Categories: Transgender & Crossdressers, Author: byWhyNotUs 

    ... just about everyone there, including my soon to be roommate Ben. Jen had made me up so well that no one recognized me. They thought I was one of her friends, dressed up in a slutty outfit girls like to wear on Halloween.

I had a soft voice and Jen thought it was hilarious for a guy to hit on me and then reveal my real identity. I didn’t mind it, because it meant I could spend more time with her during the party. We were drinking and having fun, and I was hoping something would happen afterwards.

My hopes were dashed when a new guy started to hit on me and out of the corner of my eye I saw Jen making out with another guy. I was so distraught that I excused myself to go to the bathroom. I took some time to compose myself and then I heard Jen knock on the door.

“You ok in there?” She asked.

“Yeah, be out in a sec,” I said.

I opened the door to see her waiting for me.

“Hey, I just met this cute guy and he’s gonna take me home,” she said, “Are you ok to drive yourself home?”

“Yeah, I’m good,” I said.

“Perfect,” she said and kissed me on the cheek. “Oh, I left a bag in your trunk with some surprises inside in case you’re interested in having some more fun.”

I wasn’t exactly sure what she meant and just said, “Thanks.”

Since my hopes of hooking up with Jen were gone, I said my goodbyes and drove home.

The bag inside the trunk was pretty big and I brought it inside. I was a still a little buzzed and exhausted. It took me a minute to get my dress off ...
    ... and started to remove my lingerie. I took the bra and stockings off and decided to sleep in the panties. That was the beginning and I’ve slept in panties ever since.

The surprise bag contained exactly what you thought it would. There were several bras, panties, and a red dress that matched the black one I had worn the night before. Lastly there were some cosmetics and a dildo. On top there was a note:

“Babe, I knew you would look so hot dressed up that I figured you’d want some things of your own. If I’m totally wrong, just donate them and get a tax write off. I’m pretty sure I’m right though! XOXO Jen.”

I was totally surprised. Why would she think I would want to play around with women’s underwear? I’ve been trying to hook up with this girl and she was buying me lingerie instead. I was very confused. Then I looked down to realize I was still wearing her thong from last night and it was barely containing my hardon. Maybe I did like this stuff.

Just in case, I buried everything in the back of my dresser drawers and hung the dresses in the corner of my closet and hid them as best I could. I certainly had no intentions of using the dildo, but I kept it anyway. I lived alone at this point, but I was still being cautious.

It took me a week of twisting and turning in bed before I tried sleeping in panties again. She had given me 5 pairs, which of course wasn’t enough. I went on Amazon and before I knew it, I had 30 pairs, one for each day of the month. I only wore ...
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