1. Roommates Adventures After the Snow


    Date: 6/2/2024, Categories: Transgender & Crossdressers, Author: byWhyNotUs

    ... couple touchups with what I had in my bag. Jen had told me I shouldn't really wear makeup to bed, but Ben had insisted I wear at least a little when I slept in his bed. Sleeping with Ted was new territory and I wanted to look my best for him.
    
    I checked my phone to see Ben had responded.
    
    He texted: "Of course it's ok. Have fun!"
    
    I was relieved. Not only was he not mad, he seemed ok with it, just like Jen had said he would be.
    
    I replied: "Thanks. See you tomorrow."
    
    I walked out of the bathroom still naked. Ted had a t-shirt sitting on the bed, with my panties folded neatly on top of it. I saw a confused look on his face as I watched his eyes go in between my legs. My clit was essentially shriveled after cumming three times, so he wasn't looking at that.
    
    "Hey Beautiful, what's that?" He said as he pointed in between my legs.
    
    Oh crap, he spotted the string from my tampon.
    
    "Nothing," I said.
    
    "No I see something. Did you put a tampon in?" He asked.
    
    "Yes," I said, shyly.
    
    "Wanted to keep me inside of you, huh," he said, giggling.
    
    "Don't be gross!" I said, "I was trying to be nice and didn't want to leak all over your sheets!"
    
    "I think it's hot! Most girls wouldn't be that considerate. You may be the perfect woman!" he said.
    
    I blushed. Ted was so sweet. My relationship with Ben was still mainly physical, but one night with Ted had me swooning.
    
    "Aww, you're sweet. But I think you wore me out, I might fall right asleep," I said.
    
    "I'm ...
    ... kinda beat too," he said.
    
    I pulled on my panties and put on his t-shirt. It had been forever since I wore a t-shirt and it felt strange against my body. Especially the way my boobs stuck out in the front. I had never worn a shirt like this with breasts before. At least the panties felt normal, since I had been sleeping in them for almost two years now.
    
    I got into bed and gave Ted a long kiss on the lips.
    
    "Thank you for tonight," I said.
    
    "No, thank you. I'm so glad I met you!" he said.
    
    I typically slept on my side so I rolled over. He rolled behind me and cuddled me. All the times I had slept in Ben's bed, we would pretty much stay apart. Most of the time I would wake up with his hardon rubbing against me, but sleeping was nothing like this. Ted held me in a loving embrace as we slept.
    
    I woke up first and he was still holding me. It felt so nice to wake up this way. One similarity was that his morning erection was pressing right into the small of my back. I slid myself up and his dick slipped in between my cheeks. Then I remembered I was plugged. I also felt a little sore, and thought that having sex again so soon might not be the best idea.
    
    I was used to giving a morning blowjob, so I decided to do that. I carefully slid myself out of his arms and crawled under the covers. I caught his dick with my mouth and started to suck him. I was usually able to blow Ben for a while before he woke up, but Ted woke up right away.
    
    Once he realized that the moisture on ...
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