1. Snowed In Roommates


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

    ... underneath it. I started to get nervous. We were both straight guys and I just liked the way panties felt in my bed. Now I was fully dressed again and didn’t know what I was walking into.
    
    I put my heels on and walked in them easily enough. He must have heard them clicking on the wood floor and he finally came out of my room. I peeked in the doorway to see all of my panties scattered across my bed along with the bras Jen had bought me.
    
    “Dude was all of this necessary?” I asked.
    
    “Yes it was Sweetheart,” he said, “And may I say, you look as hot as I remember.”
    
    “Gee thanks,” I said.
    
    He led me to the couch and we both sat down.
    
    “So why didn’t you tell me you liked to cross dress?” He asked.
    
    “Because I don’t,” I said.
    
    “The thong riding up your ass crack that I saw this morning says otherwise,” He said.
    
    I took a deep breath and said, “It’s just panties, I like to sleep in them. They’re...um…really comfortable.”
    
    “What about the other stuff you have?” He asked.
    
    “Jen left it for me after Halloween. I kept it all because…well, I’m not exactly sure,” I said.
    
    “Like I said, you look hot all dolled up. I wish you told me. I’ve always had a thing for girls with a little extra,” he said.
    
    “And I like girls, girls. Like I said, I just like to wear the panties to bed,” I replied, trying to convince him.
    
    As soon as I finished speaking, I felt a twitch in my dick. I tried to think about anything else, because I didn’t want to get an erection. Just then ...
    ... there was a loud pop and the power went out. It was still day time, but since the snow was covering the windows and there was no sunlight, it was pretty dark. Ben got up to get some candles to brighten the room. I had no luck in calming my erection and a put a pillow on my lap as my only hope of concealing it.“What’s with the pillow? Are you cold or something?” He asked.
    
    Totally embarrassed by my now completely hard dick, I could only get out, “Ummmm.”
    
    Not satisfied with my answer, he grabbed the pillow and threw it on the floor. Through the light of the candles he could see the tent sticking up through the fabric of my dress.
    
    “I knew you’d be into this too!” He said.
    
    “Ummmm,” I said again.
    
    “Listen, we’re snowed in with no power. I can’t think of a better time to do a little experimenting. Can you?” He asked.
    
    “Dude, I don’t know…” I replied.
    
    “You can’t tell me you haven’t thought about it,” He said, “How long have you been wearing panties to bed?”
    
    “Over a year,” I said, reluctantly.
    
    “And how many times have you played with your dildo?” He asked.
    
    “What?” I said, surprised, “Never!”
    
    “Then why do you have it?” He asked.
    
    “Jen got it for me, but it’s been in the back of my drawer until you took it out today,” I said.
    
    “Sure,” he said.
    
    “I’m serious,” I said.
    
    “Ok, I’ll take your word for it. Seriously though, you’ve never thought about hooking up with a guy while you were wearing your panties? I’ve never seen you bring a girl around,” He ...
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