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Roommates Still Snowed In
Date: 12/30/2023, Categories: Transgender & Crossdressers, Author: byWhyNotUs
... me!" She said. "Hey! I was about to make my move on Halloween, but then you met that guy," I said. "You mean the night I put you in my underwear and dressed you up like a hot chick?" She asked. "Yeah," I said. "You thought that dressing up like a woman would turn me on?" She asked. "Well, yeah," I said. She started laughing. "Sorry my friend, but I'm attracted to manly men. I sensed something about you and based from semen leaking from your ass, I was right," she said. I hung my head in shame. Ben started to rub my shoulder and said, "Take it easy, Baby. We're both here to help you. No judgments." "Yeah, ever since I kicked my fiancée out for sleeping with anything with a pulse I've been looking for a project," she said. "I'd love to help you two out." "That's why I called," he said. "Just so we're clear, I'm still attracted to women," I said. "Sure you are Sweetie," she said, sarcastically. "I'm serious. If you were here I'd fuck your brains out!" I said, trying to retain some masculinity. Jen and Ben both started laughing hard. "What? I'm serious," I said. "Oh Sweetie," she said, "I'll tell you what. Take a month to figure things out. Enjoy the clothes and more importantly enjoy Ben's cock! I hear it's huge! Then after four weeks if you still want to, you're welcome to...how did you put it... 'Fuck My Brains Out'. "Yeah?" I asked, curiously. She laughed some more and said, "You have my word. Although I bet you won't ...
... want to." "I bet I will," I said, confidently. "Ok, can we get back to the task at hand?" Ben asked. "Sure, Ben tells me you agreed to wear sexy outfits for him around the house," she said to me. "Yeah I think that's something I said yes to," I replied. "You sure did," Ben said. "What about some panties at work?" Jen said with a smile. "No way, I can't risk losing my job," I said, sternly. "We can talk about that another time," Ben said. "Ok," she said, "I hear you have plenty of panties anyway." "Yeah, 30 pairs," I said softly. "Whoa, you really added to the things I left for you. Can you go get all your bras and panties so I can see them? I'll do my best to make matching sets," she said. I stood up and walked slowly to my bedroom. The pounding I had taken was starting to take its toll and I was sore. Jen noticed me walking gingerly and said, "Damn Ben, you really broke her in, huh?" "Oh yeah, she took everything I had like a champ. Thank God for the blizzard," he said, and laughed. "One day you're gonna have to give me details!" She said. "I'll do you one better. When the snow clears and all the packages arrive, you can come over for a fashion show and then watch our extracurricular activities!" He said. "Mmmm, I would love that!" She said. I walked back in with my pile of lingerie. Jen asked to see each pair of panties that I had bought on my own. I showed her the tags so she could find the colors of the matching bras. ...