1. Roommates Still Snowed In


    Date: 12/30/2023, Categories: Transgender & Crossdressers, Author: byWhyNotUs

    ... Black Mini Skirt. She put a 4" pair of Black Heels on my feet. She led me to the Living Room where Ben was sitting and waiting for me. It took a second to get used to the extra height on the heels, but they weren't too bad.
    
    "Wow!" He said. "You look just like my secretary!"
    
    "You two picked this out. I was wondering why you bought all those dresses and skirts," I said.
    
    "Well, I figured you didn't want to be walking around the house in just lingerie all the time. I don't know if I would be able to control myself and I would be all over you constantly," he said.
    
    "That makes sense," I said.
    
    "Plus on the weekends you're going to be dressed the whole time, so you need some variety. Once you find your own style, you can order some more things on your own," he said.
    
    "Okay," I said.
    
    Jen led me back into my room and we tried all different combinations of blouses and skirts. Each time I would walk into the Living Room for Ben to check me out. Then we moved onto the dresses. She saved the tiniest dress for last.
    
    Before putting the last dress on, she had me change into a Strapless Black Bra and Thong. Then I stepped into a short Black Mini Dress with spaghetti straps. The dress was so low cut I thought the nipples on my fake breasts would pop out. The dress barely covered my ass and clung tightly to my body. She had me sit down and helped me put on the pair of strappy 6" Pink stilettos. When I stood up I almost fell over. Jen had to catch me.
    
    "You see what girls ...
    ... have to go through to look beautiful?" She said.
    
    "I don't know how you do it," I said.
    
    She had me take a couple laps around the room before walking out. I was taking extra short steps. Between the heavy things on my chest, the tight dress and heels, I had no choice. I stood in front of Ben and put my hand on my hip like I was posing for him.
    
    "Just wow!" He said. "Nicole you look smoking hot! And Bravo Jen, you've been such a great help and your color matching is amazing. Her lips even match her heels!"
    
    "Anything to help my friends," she said.
    
    Just then the doorbell rang. I didn't have time to leave the room, so I sat on the couch with Jen while Ben got the door. The pizza delivery kid was probably not much older than 20. Ben fidgeted with this wallet and moved to the side, giving the kid a perfect view of us on the couch. I knew Ben was doing it on purpose, but there was nothing I could do about it.
    
    "Gee Mister, may I say you have some beautiful ladies inside. I guess you're going out later," the delivery guy said.
    
    "Oh no, that's just how my girls like to dress around the house. If you want to come back after your shift, and have some fun with them, you're more then welcome!" Ben said.
    
    The kid's cheeks turned bright red in embarrassment.
    
    "Thanks...but...I have...a...girlfriend," he stuttered, probably lying.
    
    "No problem," Ben said.
    
    He paid him and closed the door. He walked towards the kitchen carrying two pizza boxes.
    
    "I can't believe you ...
«12...141516...19»