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The Best Kind of Trouble, Part Three

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The Best Kind of Trouble, Part Three by MWhen I woke up, it was still dark. Emily must have been sleeping lightly because she woke up soon after. Without words we gave each other a hug. Then, she got up, went to the bathroom, returned with her face and hands washed, holding a warm wet hand towel. With that she silently washed my stomach and groin. I was reveling in her scent, which now included a patina of after-sex. Climbing back into bed, snuggling up, against me, I wrapped my arms around her as she kissed me with a lick of her tongue across my parted lips. I ran my hand through her hair, noticing how soft and full it was. It seemed like a funny question to me when she asked, “Are you enjoying yourself?” Without thinking, the answer I gave was, “I’ve been having a blast!” Emily laughed out loud. I knew right away what she found funny about it and I chuckled, too. “That was such a turn on, hearing your memories of you and Sheila. Is that what you feel you’ve been missing in all your relationships?” “Sexually, yes, I guess so,” I answered. “You weren’t in love, though?” she wondered aloud. I told her more about Sheila and I, how we eventually moved on to other interests. “So, what about you?” I asked.Emily still had her head resting against my chest. But, I could feel that she smiled. “Hmmm. You’re right. It is my turn. Are you sure you’re ready for it?” Her fingers lightly tapped my withered cock and it slowly started to grow again. She let her fingers dance around my ball sack, finger-walking back up the shaft. My cock grew more, and quickly. “It seems like you are ready. Huh?” I could feel her face smiling again, against my chest.“For a long time, I never had boyfriends. In high school, most of the guys seemed insecure, immature, or they were jerks with the girls they went out with. I was always shy and clumsy around guys I did like and none of them ever approached me. “One of the reasons I liked your story so much,” she continued, “is because I have been masturbating one or more times a day since I can remember.” She laughed at herself then went on. “Just because I’m shy doesn’t mean I’m don’t get horny. You know what I mean?” I nodded, “Uh huh.” “I mean, I just can’t help it. Heck, I love it. And, I think, in a way, because it’s the biggest part of my sex life (even if I am in a relationship) it’s what works the best for me.” I had to admit to her that I knew just what she was talking about. “But,” she went on to say, “not one guy has ever been into it as much as I am. I mean, I got a couple of them to do it with me, once in a while. But, they never really got into it. Oral, they like. Jerking off, they think is a poor substitute for sex and usually embarrassing.” As she was speaking, I had the sense that Emily was being unusually candid with me. I had the feeling that she was saying things she had never told anyone else before. That was true for me, too, when I was telling her earlier about Sheila and I. I had never really spoke about it that way before because I don’t think I ever fully realised what I felt about it. My cock was fully hard and Emily’s hand continued the gentle finger-massage that I had already come to know she did so well. It felt so good, drawing out the foreplay for a long while. She went on to tell me that she has really only had four boyfriends in her life. The first was very nice, very smart, but very straight. Sex was short, sometimes intense, and that he only fucked her, never anything else. She never tried anything else with him. They ended after only six months. The next guy was a musician. He got high a lot and she didn’t like that. But, he was the most playful of them all. She told me how he loved for her to give him head while he straddled her chest. He would then cum on her breasts or her face. But, he never came that much. Maybe, it was the pot, she hypothesized. That relationship lasted more than a year. But, he went off to play in a band somewhere and they never saw each other again. She wasn’t that broken up by it though. She continued to play with my dick. My own fingers tickled her nipples which I could tell she liked that a lot. I was getting more and more hot. She went on with her story. The next guy was a jerk who cheated on her and she said there wasn’t much to say about him anyway. And, the last guy, who she was with for three years, was the closest to satisfying her. He was romantic and fun, especially in bed. He gave great oral sex and loved her giving it to him the most. But, he thought masturbating was completely ridiculous. Why touch yourself when someone else would do it for you, was his attitude. And, he didn’t like it if she touched herself, even when they were having sex together. But, none of that really mattered to her because she really loved him for everything else. Like her musician lover, he loved for her to suck on his dick and then cum on her breasts. He would never cum on her face, though. He thought that was too dirty. Emily told me that for a long while she thought this was the guy that she would marry. As it turns out, he hurt her terribly when he told her that he did not have the feelings for her that would lead to marriage. That was over a year before and she hasn’t even had a date since then, mainly because she wasn’t really interested in anyone.“Then,” Emily said, “I met this really cute guy. The moment I saw him …” she paused. Then, with a little laugh she started again, “The moment I saw him, I got clumsy. And, by that, I mean I got wet.” We both laughed. She raised her head and gave me a peck on the cheek while her hand gave a squeeze on my cock. Suddenly, I realised she was talking about me. “Tell me more,” I requested with a grin.“Let me tell you about the most sexually arousing memory I have … before tonight, that is.” It’s the one that I most often think about when I’m doing myself.” I felt a surge in my groin when she said that and her dancing fingers wrapped around my cock. She slowly started stroking me as she started her story. “When I was a teenager, about 15 I think, I accidentally caught a boy masturbating. It was after school. I went back in to get a book I left in the band room. As I was looking for my book, I noticed someone in one of the practiced booths that are along the far wall of the room. The door was closed but I could see through the window that this boy was leaning against the table. “The, my eyes grew wide when I realised that his pants were open and he was stroking his dick. He didn’t see. The lights weren’t on. So, I tiptoed behind the piano and watched. I could clearly see his hand sliding up and down. He was looking at it. I couldn’t hear him but I could tell he was panting. I had never seen a guy’s penis before. It looked a lot bigger than I had guessed it would be.” Emily was stroking my cock faster now as she was getting more and more into her story. Her body would twitch now and then, either from her other hand on her pussy or from me playing with her nipples. “I got so horny watching that guy as he beat off. I imagined kneeling in front of him, watching up close. I couldn’t help but stick my hand inside my panties and start secretly masturbating along with him. It didn’t take long before I clearly saw his cum shoot out from his dick. It was a long white stream that just suddenly shot out as he raised his hips off the table. The picture in my mind of kneeling up close in front of him suddenly turned to imagining his cum shooting onto me, specifically onto my face. That was the first time I ever thought about such a thing and it turned me on incredibly. I immediately had the biggest orgasm of my life … up until then.” I was panting heavily now. Emily was stroking my shaft and she knew I was going to blow any second. Just as she had twice before, she lowered her face to take the top of my cock head between her lips. At that moment I lost all control and blew five more shots of cum into her mouth and all over her lips, chin, and both of her cheeks. Three times in less than 12 hours she and I had the most intense orgasms together. In the months to come, there would be many more. We did lots of different things together that I will tell you about later.

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