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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. I want to start by saying that if you are a member of the morality police, you should stop right here. I was an asshole at the time with one thing on my mind. Ive seen a few complaints about cheating and whatever else doesnt fit someones moral compass in the comments here and will say that the beginning of this is not much better. It was pretty damn hot, though. Here goes, names changed to protect the innocent. I was living with my girlfriend, Rae, and (female) cousin at the time, and my relationship with my girlfriend was coming apart. Nothing that anybody did, just typical stuff that happens in the early years of being an adult when you find out which direction you want your life to go. She turned 21 and was interested in going out to the bars, I was not old enough and probably wouldnt have gone anyways since it doesnt really interest me. My only complaint about her was that she didnt like anything that wasnt plain missionary sex, so she was a little boring there, but I was willing to deal with it. She loved to talk the slut talk, had plenty of stories about things shes done in the past, but just never seemed that wild or interesting when the time came. She was the one that I lost my virginity to, and who (uninterestedly) gave me my first footjob, but really she usually wasnt all that interesting in bed; which is why there arent many stories about her on here. There are a few, they will be here someday. Rae pretty much comes up to me after a weekend back in her hometown and says something to the order of I think I like someone else, I want to go to an open relationship so I can check out my feelings for this guy without cheating on you. Always about the technicalities, it seemed with her. This was an ongoing thing, having to ask the right questions and use the right words to get what you wanted to know; but thats a discussion for another sub. I knew this meant that we were within the final days of this relationship, so I agreed, not really thinking that she would come back, but wanting to be able to say I tried and maybe I would prove myself wrong. A part of me just wanted this to be over so I could move on. Since I already knew things were over, I could only win at this situation, right? So, she goes back to her hometown for the weekend, and I stay in the apartment. I kind of chill for the first day, hanging out with my cousin; who lets me know that shes not going to stay friends with my girlfriend after this, no matter what happens. She then asks if it would be weird if she invites my Jess (my ex, the girl from the first handjob story) to hang out and stay the night, since the two were good friends and had some sort of plans. I said it didnt really matter to me, we were young when we dated and are both over things by now. Jess comes over, I talk to her a little bit but nothing too crazy, and go to bed. It was pretty clear from talking that she still liked me, and that she still had the fun personality that I really liked the first time we dated. I got that awesome feeling that you get when an ex still wants you but you think you have moved on to better places, despite the fact that my girlfriend was out doing who knows what with some guy. Not trying to be mean here, but this was my first time seeing my ex since we broke up, and she was not in the same condition I left her in. Where before she was a little chubby in the right places, now she was huge. Like couldnt fit in my car without lifting up the armrests that split the bench huge. She had also chopped her hair off into an ugly version of a European short girls haircut, like she was trying to be edgy but didnt want to put in the work to keep it looking proper. But, she had thick, librarian style glasses and a piercing in the side of her nose, both pluses in my book. Her face made me attracted to her, even though I wasnt really attracted to the rest of her. Somewhere around this point I switch which head I think with; I woke up at ~6am with a different frame of mind. Im not sure if I dreamed of doing something with her just before waking up or what happened, but I had sudden urges that needed to be met. Knowing that she was still out there crashed from the night before, I sent her a text: Hey, Im pretty sure I was dreaming of you last night. Want to come in here? Holy fuck, I never do anything like that. I wonder what will even happen. Worst she will do is think Im a perv and tell me to fuck off, at which point I doubt Id really care. I heard her phone go off in the living room, so I know she has the message. So now, we just wait. Or not, she replies back almost immediately: Sure, be there in a minute. Are you okay with this being just a one time thing? I quickly responded. Yea, sounds fun, she sent back. Well, that was easy, I thought. Ill admit I had a few seconds of guilt here about what I was doing since my girlfriend and I had not broken up or talked about what was next, but if she wanted open she was going to get open and she was going to like it. Jess came in the room and laid down on the bed next to me. She was wearing thin pajamas, no bra under them, and it was pretty obvious that I had just woken her up. Knowing that there was no way she would say no after coming in here, I went in for the kiss. She kissed back, and we made out on the bed for a few minutes. Her lust for being physical hadnt changed either, this was a more intense makeout session than I had had in a while. She slid under the blanket with me, finding that I was already naked (I sleep naked). She slides in close, my dripping cock rubs on her pajama pants making a wet spot from the pre-cum. Remembering my training from our relationship together, I slip my hand down the front of her pants and begin rubbing. I barely have a minute in and she asks me to stop because shes finished. I see that this hasnt changed either, since there was no way I was doing anything very intense for that minute. She says You have to get something out of this too. Ive always loved the way she thought, and Im struggling to remember why we broke up. Wait, I remember, but it isnt relevant to this thread. I have a strange request I reply. Whats that? she asks. Ignoring the obvious bad joke of giving an explanation about what a strange request is, I reply I want to cum all over your tits. Thats not really that strange, or even a big deal, she replies. Again, fuck, why did I ever leave this? Well, Rae wouldnt let me, I guess Im just used to being told no, I say. Without hesitating, she unbuttons her pajama shirt and tosses it off of the bed. Her tits are exposed, and while I remembered her having D size boobs in high school, in the two years since they have grown to somewhere between DD and the next size up. These were huge! She does a quick scan of the room. She must know me well, knowing that there is no way that Id not have some sort of lube within reach of the bed. She spots the KY tingling lube and grabs the bottle as I roll onto my back and kick the blanket off of me. She squirts a bunch all over my cock, and the minty smell of the lube fills the room. She uses the palm of her hand and begins rubbing and spreading the lines of lube all around. The coolness starts kicking in, and it feels like a slight breeze is blowing over my cock. She goes from rubbing to grasping and stroking my cock slowly, and adjusts so that my cock is pointing right at her boobs. Jess was always the girl I remembered for giving the best handjobs, and this one was no exception. I couldnt even describe what exactly she does, but something about her touch, anywhere on my body, was always amazing. Her touches were even better when they were on my cock with lube. Her handjobs never lasted very long, and this one was no exception. I exploded all over her chest, and as the spurts came out she moved my cock around to thoroughly cover both of her tits. I wish that I had asked to see our work, but in the position she was in I couldnt see it, and she rubbed it all into her skin before I got a chance. When she turned around, all I could see was the sheen of wet tits that smelled like the lube. She put her shirt on and buttoned it back up. What now? she asked awkwardly. Do I stay in here? I said No, you should probably go back out there so %cousinname% doesnt see youre not there. I realize now that that was an asshole move, but she goes back out to where she was sleeping. I go back to sleep. A few hours later, I get a text: I smell like you, that was pretty fun. I send back, across a few messages but you get the point Im not looking to date or anything, but I kind of want to do this more. We both know and trust each other 100%, we could help each other do things we always wanted to do. She replies that she would like that. This was going to make my breakup a lot easier. As a spoiler, though, she never requests anything, and never has anything in mind when I ask if she wants anything. Everything we do ends up being more for me after she gets off from me rubbing her. sadorhappy