I asked her "Diane, are you sure you want to do this?" Yes, Mike, I'm sure. But thanks for asking.", she answered, pleased by my question.Holding myself in place with one hand, I put the other on her hip to steady myself as I gently pressed forward. I could see it as my efforts pushed the ring of her anus inward, but it wasn't enough to get me THROUGH - I was simply too reluctant to risk actually hurting her. I eased up for a moment, then tried again, with a little more pressure; still without success.Diane, recognizing the problem, told me "Mike, it's okay. I want you to do this. If it starts to hurt or anything, I promise I'll tell you."Reassured that she really did want it to happen, I realized that I could do what I'd done the first time I'd deflowered her: simply scan her, continuously, so that I'd know if/when I was hurting her. With that in mind, I took a deep breath, got into her mind, and started pressing myself against her.From her mind, I knew that it was uncomfortable for. She just wanted to see Mom,” I replied. “OK, so now we can have fun all night?” Jennifer asked, and by fun she meant going out, getting drunk and then end up having sex in the back seat of the car. I never had sex with a random guy in the backseat of the car, but I had driven the car while Jennifer was sucking and fucking random guys in the back seat. Once I sucked a random guy at a party and he ruined it by cumming in my mouth. At that time, I didn’t like swallowing or having cum in my mouth, but I had since learned to love it. “I’m not sure about going out tonight,” I said, because tonight I had plans to get fucked in the ass by my dad. “And where are my notes?” she asked and I handed the notes to her. “Oh my God, thank you so much, Jenny,” Jennifer said and hugged me, pressing her big boobs on mine. Jennifer and I never had a full on sexual encounter with each other, but yes a couple of times, we had kissed and touched each others’ boobs. While she was checking out the notes, I.
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