1. My Life with Tess McGregor Ch. 02


    Date: 6/19/2024, Categories: Transgender & Crossdressers, Author: bymembrain

    ... Also, the bra couldn't keep her tits from letting me know they were there. Her brown hair cascaded in large waves around her face and just past her shoulders. She never seemed to wear a lot of makeup, just enough to highlight her delicate features. Tess had full lips and a cute nose. Her eyes shined a pretty green and her naturally long lashes accentuated their glint.
    
    I was proud to be sitting with her. She snuggled up against my right side and playfully used her hands to touch me in a way that sent shivers down my spine. She was very distracting. I couldn't help it, my mind was busy thinking about her sweet voice as she looked at the menu and talked about what looked good and what she wanted to order.
    
    She apparently had made her decision as she pushed the menu aside and wrapped both off her arms around my right bicep. Her face was close to my shoulder and she pulled my right hand over to rest on her left thigh.
    
    "What are you going to get?" She asked while she was feeling my bicep.
    
    "What... oh, umm. I haven't even looked yet." I said as I glanced down at her sweet face with her eyes looking up as if to say, 'Silly Brad, am I bothering you?'
    
    "Well, here comes our server, you better hurry, because I want to order. I'm hungry."
    
    "Ok, you go first."
    
    After we ordered I moved my hand up her thigh, feeling her soft skin. I reached the small bulge at the top of her thighs and gave a little rub.
    
    "Be careful, Honey, I don't wanna cause a scene if you give me an ...
    ... erection."
    
    "Oh. Yeah, you're right. Sorry."
    
    "That's ok. That's why I'm wearing a skort. It does a good job of hiding me without having to do a full tuck. But, still, sometimes if I get really excited, it has a tendency to show."
    
    "OK... God, you make me want you so bad. You turn me on just sitting here."
    
    "Hmmm, that's nice to hear. I confess, I feel the same about you. I love the way you're so turned on by my girl-cock. It makes me want you too... Here comes our food!"
    
    After we ate, Tess moved back to snuggle up next to me.
    
    "Hmmm, that was good. Their pancakes are delicious."
    
    The whole time we were eating, I couldn't stop thinking about fucking her. When she snuggled up to me again, I put my hand back on her silky thigh.
    
    Finally, I said in almost a whisper, "Tess, I think I wanna try... um... anal."
    
    "Well, you already di... Oh... OH! I see."
    
    She squeezed my arm and tried to get closer. I could tell this made her excited.
    
    Tess moved her face close to mine and said, "I would love to be the one to pop your cherry, Brad." She giggled and I raised an eyebrow at her comment. Then I smiled as she said, "When we get home, let's change into something comfortable at my place."
    
    On the drive back to the apartment, Tess sat close to me. Her hands were busy rubbing my cock the whole time. After we parked in the garage and I turned off the motor, we kissed while she continued to rub my cock through my pants.
    
    I broke away and said, "Fuck, Tess, you're ...
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