1. Caught in the Crossfire


    Date: 9/9/2015, Categories: First Time, Taboo, Voyeur, Author: brianbigdogsmith, Rating: 100, Source: xHamster

    like that." "I'm more innocent?" She sighed. "Now you really have to do it. I have to prove to you that I'll do anything. I want you to have anal sex with me." I shook my head. "But you've never done it before. I don't want to hurt you." "If Erika can learn to take it, I can learn it too. C'mon. I want to show you that I love you, and I want my first time to be alone with you, without her." "You don't have to do it to prove anything." She spread her legs and took my hand, pulling it to her crotch. My fingertips brushed against her pussy, then her ass. "Don't try to talk me out of it. C'mon, don't try to deny that the idea turns you on, doesn't it? You want to do it with me?" I thought about it, and nodded. "Yeah, I admit the idea turns me on. But I still don't think it's a good idea." She rolled away from me in the bed, giving me a kiss then standing up and leaving the room. When she reappeared, she had a pat of butter in her hand. She knelt over me on the bed, sucking my cock to full hardness, as she played with her own asshole with slippery fingers. She took her time, trying to relax enough to get her fingers inside herself. Finally she decided she was ready, lubed up my cock with buttery fingers, and moved up to kneel over me on the bed. My cock was sticking up at an angle, so she tried lowering her hips down on me. The head of my cock brushed against her pussy, then her ass. She tried to get it into her ass, but it kept slipping one way or the other. "Hold yourself ...
    steady." she instructed. I reached down around her hips and held my cock firmly. She shifted her weight and got herself lined up, the head of my cock pressing firmly against her back entrance. Finally, the head popped through. "Oh!" she gasped, a worried look on her face. "You don't have to do this." I said again. "Shut up." she said softly, shifting herself, trying to find a more comfortable angle, trying to relax and let me in. It took several long minutes, but she finally succeeded in getting nearly the full length of my cock inside her incredibly tight, hot, virginal ass. "That's good enough" I said soothingly. She lowered herself to my chest, kissing me, and allowing herself one small smile of victory, along with the discomfort. "Will you come in me, like this?" "I think I need to move a little, in and out." She looked worried, but nodded. Very carefully, I rocked my own hips, pulling back slightly then pressing myself up her ass. She grimaced, but I didn't dare try to stop. Her determination, and my own lust, kept me going, as I cautiously ass-fucked her from below, moving faster and faster, trying to ignore her gasping and keep going, until finally I came. Carefully, I pulled out and she pulled away. There was a single tear on her cheek, and she moved awkwardly as we went together to the shower to wash off. Under the water, I held her and kissed her and caressed her body. It was a big event for both of us, and we spent hours together afterwards, cuddling and talking it over. ...