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This is a series of stories about hooking back up with Jess, my first HS girlfriend, after two years with someone else. Here goes, names changed to protect the innocent. Check out parts 1, 2, and 3, and my "First Handjobs" series for more from the same girl. The summer went on, and through my internship turning into a new job, things at work requiring crazy hours, and Jess's own work stuff, we saw each other less and less. I think we both knew that we weren't going to do this for much longer. Still, when we had free time we always checked what the other one was doing. One nice warm day, a day that was still humid and wet from thunderstorms the night before; she said I needed to come over so she could show me something. I don't know what I thought she had to show me, my thoughts went to some sort of damage from the storms the night before. I don't know what she wanted me to do, and her parents were rich so surely they'd call someone to fix whatever it was, but I went over anyways. She said that she just wanted to talk, so we went for a walk around her neighborhood. Her neighborhood was a long road that branched off of a two-lane county road. This long road ended at a cul-de-sac where her house was. Lining the entire length of the road were large houses; an island of upper-middle and upper class suburbia in an otherwise rural area. While a younger me, a slim shady wannabe always felt out of place here; the new, mature, career oriented me took the chance to look around. Maybe I'd buy a house in a place like this someday. Naw, too many busybody neighbors getting all up in your shit. I daydreamed randomly while she talked until one question broke my distraction. "Do you like my pedicure?" she asked me. What a crappy foot guy I was, I looked down and saw that her feet were absolutely perfect. This wasn't a cheap job, she went to a pro. They looked so smooth and clean, with blue and white toes. I just wanted to ravage them right there. She was also wearing brand new blue flip-flops, the cheap kind with the plastic top that formed a triangle between the first two toes and each side of her foot. Somehow I didn't even notice until she mentioned it. Am I really not horny at all? No way. I told her of course I did. We walked to the edge of her neighborhood and crossed the county road that separated her neighborhood from the more rural area. Across the county road was a smaller two lane road, which we followed for a while. We were pretty far from the houses in her neighborhood at this point, and the road we were on went to a wooded area. We continued talking as we walked up a big hill, but really I was distracted by her feet, which now had red marks on the top from walking the long distance in hard plastic flip flops. I could kiss those red marks better, I kept thinking. And lick the rest of her feet better just to make sure. When we got to the top, she asked if I remembered where we were. A flood of memories came back to me that I had otherwise forgotten about. When we dated in high school, if it was above like 30 degrees, we would go for walks to get away from her parents. One time when walking up here, we stopped; and she opened my pants, pulled out my cock, and jerked me off. This was another one of my first handjobs, but wasn't exciting enough to stand out in my mind until being here brought it back. I remembered what the cold air felt like on it until she got her warm hands around it. I remembered that we didn't have lube and didn't think of using her spit, so it felt rough until some precum wetted things up a bit. I remembered her turning with her back towards me, her hands still on my cock, to hide what we were doing when a car came past. But she didn't stop stroking. We probably looked like a couple of dorks to whoever drove past, her standing there and me practically crawling up her ass trying to hide my nudity. And I remembered her moving so I didn't get cum on her clothes as she jerked me to completion, leaving a little puddle on the side of the road. After I finished, we turned around and walked back to her house. Her parents only saw us go out for a walk and come back less than 20 minutes later. It was the perfect crime. I miss being young, I thought to myself. "Do you want to do it again?" she asked, "for old times sake?" It was as though she knew exactly what I was thinking about. She was playing her game, knowing exactly what I was going to want before I did. "Sure," I responded, and without hesitation she unzipped my pants and pulled my cock out. She gave a few tugs before bending at the waist and taking the tip into her mouth. This was way better than the first time. She bobbed her head up and down like this a few times, teasing just my head, before saying "We need somewhere more private, let's go into the woods!" We walked back to the bottom of the hill, where the trees were a little thinner so we could get in. I followed her into the woods. She, wearing a hooded sweatshirt, loose capri workout pants that stopped just a little bit above her ankles, and flip flops, was struggling a little bit to work her way through the branches. Her nice clean pedicure and pristine flip flops got dirty as we walked in, blazing our own trail through the muddy woods. I'm usually not much of a dirty feet guy, but seeing it as it happened was quite a turn on. Still distracted by her feet, I had fantasies of this playing out to be another awesome foot fetish session. I pictured her taking off her flip flops and continuing barefoot. I imagined watching her continue through the muddy sections, the mud oozing between her toes with every step. She knows how turned on feet make me, so I know that if I'd ask that she'd have no problem stopping and playing with the mud with her feet a little bit before stroking my cock and taking a load of my cum all over her muddy feet. Maybe we'd find some berries or something and I could watch her crush them for me. Licking unknown berries off of her feet probably isn't a good idea, but seeing her mix the berry remnants with my cum would be so hot. My fantasy is short lived, though, I have to snap back into the real world to concentrate on pushing through the branches without getting caught up or hitting myself in the face with them. Branch scratches suck. Soon, we got far enough away from the road that we decided we were safe. She pulled my pants and boxers completely down so that they rested at my ankles. I pulled my shirt up to about the middle of my chest, which she responded to by gently kissing down my belly and to my shaved mound at the base of my cock. I put my hands behind my back to hold my shirt up and stood there, exposing myself to her. Her kisses continued to the base of my cock, and then up my shaft, before ending with long lick that went the length of my shaft and up to my head. My cock jolted, and I shuddered a little bit from the excitement. She knelt down, her knees on the wet forest floor, and started sucking me off. No thoughts, that I could detect, worrying about getting her pants dirty or how wet and cold it was where she was kneeling. Just 100% focus on giving me pleasure with her mouth. She started with no hands, and then added her hands and stopped occasionally to stroke me off while telling me how badly she wanted to see my cum squirt. Her light grip, combined with the wetness from her spit, made her stroking feel almost as good as her mouth did. It felt sort of surreal to me, standing outside with my pants and boxers around my ankles, her mouth bouncing up and down my dick. Like I was completely exposed, anybody who really tried could probably see what we were doing from the road. I willed this away in my mind. I couldn't think of a reason why I'd stop on the road and stare into the woods, so why would anybody else? At the time, I didn't cum very quickly from oral, and she wasn't absolutely mind-blowing at what she was doing. This was probably nerves from the new surroundings, because she had given me blowjobs before and they weren't bad by any means. I just had to make sure not to cum in her mouth, which was easy for me. I took this as a rare chance during to look down and really enjoy the show. What she lacked in skill she made up for in enthusiasm and showmanship, and she didn't seem bothered at all that I wanted to watch her work. She would occasionally look up and make eye contact before going back to concentrating on what she was doing. She would move very slowly, letting me watch her lips conforming to my cock as it moved into and out of her mouth. She would pull her head back until just the very tip of my cock was on her lips, circle her tongue around the head a few times, and then slowly work my cock back into her mouth. The wind was blowing pretty good, even through the trees that surrounded us, so she would occasionally have to stop and move her hair away from my cock and her mouth. She let out a playful giggle every time she had to do this, like fighting the hair blowing in front of her face was a fun game. It was very hard to resist just grabbing her head and going to town, but I wanted her to enjoy this as much as I was. Overall it was a very sexy experience, and eventually the feelings built up to where I was close to finishing. I hadn't noticed as she did it, but somewhere along the line, she sped up. She was moving her mouth pretty fast up and down most of the length of my cock now, rocking back and forth on her knees as she did it. I could feel her circling her tongue around my shaft, and my head pushing her lips open a little bit as she pulled me almost all the way back out of her mouth before taking me back in again. I told her I was about to cum, giving her a few seconds of warning before it actually happened. She made some sort of sound, acknowledging that she had heard me, and kept on going. The humming from whatever sound she made vibrated along my dick, pushing me closer to climax. I know that she doesn't want me to cum in her mouth, she has never been a big fan; but I just couldn't make myself stop her from making me "accidentally" do it. She'll pull me out of her mouth in time, she always has before. As I approached the point of no return, I gave her a more urgent warning. She again ignored my warning. I tensed up, clenching my muscles in that region with all of my might to try to avoid filling her mouth with cum. I just couldn't make myself pull out, I needed her to keep doing this even if she wasn't going to like the consequences. And this one will be a mouthful, there is no way it couldn't be. I'm so turned on and filled with lust. She's been awesome, I don't want to mess this up and ruin any future chance of blowjobs. Despite my internal struggle, her mouth gets the best of me and I get off. I can feel the spasms starting as I start to pump out cum. The first "pump" goes, and she doesn't react. My cock throbs in her mouth. There is no way she didn't feel it, what is she doing? Maybe nothing came out, the first one doesn't always produce liquid. She'll pull her mouth off now that she felt it, for sure. The next "pump" came and I felt a big squirt of cum leave my tip and go into her mouth. The inside of her mouth now felt very slimy and more wet than before. There was no denying it now, my cum was in her mouth. I just came into her mouth, something I know she doesn't want me to do. About halfway in between the 2nd and 3rd "squirt," she took her mouth off of my cock. "This is where she gets pissed," I thought to myself, "Why didn't I just pull it out myself?" She still didn't seem to mind what had happened, though. There was no gagging sound, no sudden outburst of anger, not much of a response at all. She aimed my cock away from her and continued stroking me while the next few shots squirted and the rest oozed out and fell onto the forest floor. I looked down and saw her hand covered with cum, with a few streams running down her hand. Some of them were building up to where they were just about to drip off of her. Another one made its way up her sleeve and kept running down her arm. I must have had a look of disbelief or shock on my face, like I didn't know what do do or say. She broke the silence by sticking her tongue out and then flirtatiously saying "See, I swallowed some of it." In that moment, she was really proud of herself for that. All I could think was wow, she learned a new trick! She said she never was able to do it without gagging before. Wanting to reward her for her awesome accomplishment, I gave her a kiss on the lips, which turned into making out with my pants still down. I could taste myself on her lips. She really needs to be careful, she's going to brush my cock along the front of her shirt and get a tell-tale wet spot. She thought it was so awesome that I would kiss her after she swallowed my cum, but honestly I just couldn't think of any reason why it should be a big deal. We fought our way out of the woods and walked back to her parents house. Her dirty pedicure and slightly damp knees on her pants had to be a giveaway to what happened, or at least where we were. This was the last time I hung out with Jess, and we only talked like one or two times after it. As I mentioned at the beginning, our schedules (and in a way, our lives) were drifting back apart. While our sexual chemistry was awesome, I didn't feel like she was "growing up" or developing independence from her parents despite being 21 years old. It was like she was still 17, which was fun for my dick, but frustrating when she would let herself be controlled by curfews or her parents taking away her car if she "misbehaved." I just didn't have it in me to try to keep us from going our separate ways. I think the feeling was mutual, because she didn't really text me back either. My last call to her was when I told her I was going to start dating someone. I don't know why I felt I needed to tell her, we both agreed to this from the beginning, but it felt like a good way to close out what we were doing. A few years later when I saw her and said "Hi," she was with a boyfriend and showing me her engagement ring. Good for her, but she had let herself go to the point where I couldn't imagine being interested anymore. While Jess was fun and I'm sure there are more stories that I will remember, the awesome stories from this crazy summer don't end here for me. I soon started dating a goth girl who was a nymphomaniac, was a fiend for cum, and had a heel fetish (a perfect trifecta). From a pure sexual lust standpoint, she's the "one that got away." Look for stories about her soon. sadorhappy