1. My Life with Tess McGregor Ch. 02


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

    ... tease her and wasn't going to spoil it all by ramming her cock down my throat.
    
    I stuck out my tongue and began a slow, deliberate assault on the beautiful pink head of her cock. Moving my tongue underneath and around, her cock bobbed up and down with tense excitement.
    
    I knew if I continued to tease her and then take her in my mouth, she would undoubtedly cum. I wanted her to hold off until she had her cock up my ass.
    
    I pulled away and put her cock back inside her panties.
    
    "Awww, you're not gonna stop now are you?"
    
    "Yes, I want you good and hard and ready to pop when you put this beautiful cock up my ass."
    
    "Oh, Baby." I stood up and she threw her arms around my neck and said, "I'm so fucking horny right now.... Alright, let's go to my bedroom." She kissed me hard, then turned around and headed for her bedroom.
    
    I still had my shorts on and the tent pole inside guided my way forward. When we got to Tess's bedroom, I yanked off my shorts and T-shirt. Tess went into her bathroom while I laid down on her bed.
    
    She came out with a bottle of lubricant and a small pink vibrator.
    
    As I lay on the bed, Tess climbed up and walked on her knees closer to me.
    
    "Brad, before I go ramming my cock into your cute butt, I'm going to help you relax by rubbing some lube on it and inserting my little friend here." She held up the small pink vibrator. "Ok?"
    
    "Alright."
    
    "When you're relaxed, I'll insert my cock slowly. I'll take my time, so you won't have any ...
    ... surprises or pain... Well, there may be some pain at first, but you'll get used to it pretty quickly."
    
    "Ok, but first, get that pretty cock of yours up here so I can make it hard again. It appears to have gone a little soft."
    
    "Oh, don't worry, it'll be plenty hard after I play with your asshole."
    
    Still, Tess was willing to comply with my order and started to take her panties off.
    
    "No, no. Leave those on, please."
    
    I remained on my back, so Tess straddled my chest. Her cock had deflated just a little, but still made a pronounced bulge in her panties.
    
    When she scooted up, putting her panty covered cock close to my face, I reached up to pull her panties down. Her cock bounced out and I caught it with my mouth. I proceeded to suck her cock. It got hard right away. I liked sucking her in this position. It was submissive and I enjoyed the feeling of her in a dominant position above me.
    
    "Ok, Honey. Any more of that and I'll cum before I get the chance to fuck you."
    
    Tess scooted back off of me and grabbed the bottle of lube. She motioned for me to turn over on my stomach.
    
    "Wait, can't we do it this way?" I lifted my legs up to expose my ass. "I want to see you while you're fucking me."
    
    "Oh! Yes. That's a wonderful idea."
    
    Tess dropped some of the lube on my ass. She put the little pink vibrator to my hole and began to rub around the outside. "That feels good."
    
    "Good."
    
    Tess started to put a little pressure on my ass and the pointed end of the vibrator ...