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I originally posted part of this to the holdthemoan subreddit, and then learned of this sub, and decided to share. When I was 16 my mother lived across the hall from a couple of gals that were roommates. One was in her 60s (Bonnie), the other in her early 30s. I go over there one day to get something, and find the younger one is putting up stringers and stuff for Bonnies birthday, while Bonnie is knocked out drunk on the couch. She asks me for help with decorating, since it needs to be finished before Bonnie wakes back up. These thoughts of the occasions when shes been flirtatious with me flash through my head. I was mostly sure that I could get her; if I could ever get her alone. But that was impossible, since my mother was smart enough to not let me be there alone with her, and Bonnie hardly ever left the apartment regardless. There I was, in a situation where we were finally alone enough to get away with stuff, but not so alone that my mother would come busting shit up. It was the perfect scenario. The best of both worlds. At first she was standing on a chair, asking me to hand her stuff, and to help her keep balance. I was holding her waist, and getting a decent view as her shirt lifted with her arms. It was a short shirt, and she wasnt wearing a bra. While I couldnt see everything, it was enough to get me going. But, what could I really do with that? I thought about reaching up for a feel, but that just seemed like an odd and presumptuous thing to do. Then, I got an idea: if I were on the chair her hands would be on my hips, and my shirt lifting to reveal ...me. So I pointed out that I was taller, and could reach stuff easier, which would help make it go faster. She agreed. I got on the chair, positioned my back to bonnie, annnd instantly started to pussy out. She had been flirty, sure, but that didnt necessarily mean that she would sleep with someone half her age. What if she flipped out? What if Bonnie saw? What if ... So, I went about being professional and simply doing what I was supposed to be doing. She was, in fact, holding my hips; just as I had planned. Which was nice. But what does that really even matter? I was just being a perv. Dont be a perv... Then I looked down to ask her for the next thing, and noticed she was staring right at my crotch. Her head just inches from it. My bravery came back. I was at half-mast, once again. I should note that at this point in my life I sagged my pants. (It was the mid 90s and I was a teen.. what can I say.) So there was only my silk boxers between her lips and my cock. I thought about simply pulling it out, but was too afraid. I had to make it like it was a mistake, in case there was an issue. So, the next time she turned around to get stuff for me to put up, I quickly pushed the opening of my boxers back, and the other flap just a little to the side, so that when I lifted my arms again my shirt would lift to reveal just a peek of the side of my bare penis. I snuck a look down, and she was looking. I was so excited. My heart was racing. We did that a couple of times, each time me pushing the other flap over just a little more. I kept hoping that she would just go for it. Make it easy on me. At some point more than half the width of my semi-rigid penis was exposed. Then, I could feel her breath, and a wonderful and horrifying thing happened: I thought for sure she was going for it, and that got me going enough that it POPPED right out, all on its own. I had pulled the flap too far! Gotten just a little too excited. The friction from the silk simply wasnt enough to keep it in. BUT... she didnt go for it! Shit, its out. And shes not doing anything, at all. What do I do?! I pretended like I hadnt noticed, and just continued looking up at my work. I snuck a peek, of course, and verified that she was, in fact, still looking right at it. Her face was closer than ever. I could still feel her breath. It became mental acrobatics. I didnt want to become hard, and get busted, or get soft, and turn her off at the sight of my super flaccid penis. Dont even ask me why I was still worried about being busted. She had to know I was up to no good. That it wasnt entirely an accident. I was just still stuck in that frame of mind, I suppose. Just then, my mother popped her head in the door. Wondering why it was taking so long... Shit, shit, SHIT. The door was in the direction of the couch, so my back was turned. Luckily, the roommate had just reached down to grab something. So, what my mother saw was me with my arms up, working away, and her digging in a box. Everything seemed normal from my mothers perspective. I was so lucky. Had I been turned just slightly it wouldnt have been just my back that she saw... Had I been more aggressive my mother would have caught us in the act. The instant my mother left I threw caution to the wind; I was about to run out of time. Any moment Bonnie would wake up. Any moment we would be done decorating. Or, what if she simply grew tired of my childish games? ... So the next time she grabbed my hips, I lifted my arms, and watched her shift her glance down, at which point I lifted my cock towards her mouth, to meet her gaze. It was like slow motion. My heart was beating out of my chest. Lips dry, stomach on a roller coaster. This was it, what would happen? Will she kick me out? Scream? Tell my mother?! What would my friends think? I almost felt like this wasnt even reality. Like I was tripping or dreaming or something. But my fears were quickly extinguished when she simply took it between her lips. Lapped it right up. Jammed it as far down her throat as she could, without so much as even looking up at me. She had been waiting for me to make my move, just like I had. There I was, standing on a chair, in the middle of a dining room, with a 60 year old lady sleeping just maybe 12 feet from me, getting one of the most intense blowjobs of my life, from someone damned near the age of my mother. Leaving one hand on my hip, she took the other gently across my thigh, then upwards under my sack, pulling them up, as she began to wrap her hand around my shaft; letting my balls slide through her palm in the process. She began twisting her hand while keeping it at pace your her lips; a good, steady pace. I could even feel her tongue moving around, pressing hard against my skin while sliding in a different pattern than her lips and hand. My heart, still going at full force, made it so I could feel the throbbing against her tongue. Feel my pulse push me larger and larger. It was like a perfect melody of several sensations all at the same time. She looked up and locked her eyes on mine, and gave slight smile. She appeared to be enjoying it. I can’t stress how much of a turn on this was. She definitely knew what she was doing. Layer in the anticipation, her abilities, my nervousness, and really just the intensity of the whole situation, and I was on a crash course. While I knew I needed to hurry, to avoid getting caught, I didnt want it to end. Not only that, but I was worried that she would think poorly of me if I finished too quickly. But, despite my every effort, it was going to happen, and soon. No matter what I thought about, I couldnt remove myself from the situation. It was just too strong. But all of maybe 60 seconds into it, just when I felt I couldnt hold it in any longer, she …stopped… Peeked her head around my waist, and took a look at Bonnie. Tucked me back in, under my waistband, and muttered that we shouldnt be doing this. The agony was unbearable. I tried grabbing her hand pulling it back, but she pulled away shaking her head, saying "we can’t." I got off of the chair and, with great disappointment in my voice, asked if there was anything else that needed to be put up. She just said that it looked done to her. My heart was on the floor at this point. Waves of dismay flooding over me. I felt like maybe I should have gone ahead and just finished quickly. I wasnt going to win regardless. I felt like maybe had I had fucked up. Made a huge mistake. She picked up the box of supplies to put them away, and I grabbed it from her hands. Asked if we should put in her bedroom. She cracked a smile at my suggestion and said something along the lines of "I should at least repay the favor of you helping me." YES! It was back on. She walked in front of me as I carried the box the bedroom, and closed the door behind me. But the door was line of site of the couch, so I pointed out that if Bonnie finds us behind a closed door she would know what was up. She agreed and opened the door back up. I asked where to put the box as she sat down on her bed. She pointed to the corner right next to where I was standing. As I put the box down, she was already pulling on my waistband. By the time I straightened myself back out, she had came forward, getting on her knees, lunging straight for it. Like she couldnt wait to have it back in her mouth. Again, I cant stress enough how appealing it was to know that she was enjoying this. I was no longer nearly as nervous. My heart out of my throat, back where it belongs. Keeping concentration to stop myself from finishing was much easier. But, I have to say, this wasnt nearly as intense or enjoyable as before. She had great technique, yes. But the moment that I was previously in was lost. Despite the risks, I wished she had just kept going in the dining room. I think this is when I discovered my penchant for risk. I had always enjoyed sneaking places with my girlfriends, sure. But I dont think it had dawned on me how much more I enjoyed that behavior over "normal" sexual situations until now. I would occasionally peek my head around the corner to see if bonnie was still laying on the couch. That part was fun. I expected that at any moment I would be pulled to the bed to make the pleasure mutual. But it didnt happen. 2 minutes, 5 minutes, 10 minutes later she was going strong. Not even so much as a break for her lips. It was blissful. She eventually stopped for a moment just to tell me that I should hurry up and finish before Bonnie woke up. She had no intention of having me return the favor. She wanted it to be just be a blowjob. This was odd, but enticing. I let myself relax, and just go with it. It wasn’t long before I was cumming. She increased her suction, and wrapped even tighter with her hand. Like she was trying to pull every last drop out of me. Wave after wave of orgasm that became more intense with each blow. She was pulling with the waves. No longer holding the steady pattern she had before. It felt like I had hadnt came in months. So much power behind each thrust. She continued even after I was done! She was in no hurry to miss a single drop, and when she finally slid her mouth off of me she stood up and said You taste so good. Right then I wanted more. But I knew I was pushing my luck. I put myself away and actually thanked her. … she giggled and told me we should do it again some time. I was smitten. I went home, and all night dreamt of what had happened. Almost even questioning if it even had. But I knew. We maintained this relationship in secret for a couple more years, until she moved away. Every time in risky situations. There was simply no way to avoid it. Not that I even wanted to — I loved every second of it. Gr1pp717

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