I warn you, this is going to be long. But I assure you, it should be interesting in the very least. I doubt any sound advice could be given, but I'd like to share this story nonetheless. I am 28.

Rewind to May 2. I had been seeing my 23 y/o girlfriend for a couple months, long distance. Things are spectacular. She comes to visit me for a week, we make the relationship official, and open. The first night we have a sex marathon, which ends with a simultaneous orgasm. The problem is, she's not on birth control and I have no condom, essentially forcing her to take Plan B. Probably one of the dumbest things I have ever done in a relationship. A few weeks later, she breaks up with me, citing this as the main reason. I am devastated. This, is my crazy ex. June 2. Crazy, i.e. legitimate mental health issues. I have my own - unfortunately for me, I am quite attracted to crazy. Sigh.

6 days later, I meet the virgin. A smart, sexy little 19 year old. Tons of IOIs and flirting. A couple weeks later, we have our first actual "date", where I attempt to kclose - and fail. She claims she moves very slowly in relationships, and just got out of a string of long term ones. A couple weeks later, we're hanging out in a group, and I swiftly execute an isolate and very good kclose. She persists to my intentions, and I admit to liking her. Then she pushes, claiming she doesn't want some kind of relationship. A small string of events happen and we have a short falling out, only to be made up shortly after where she comes to my apartment for several hours, and I end up fingering her on my bed. A week later, a similar falling out repeats itself. Definitely rollercoaster at this point, and I pull away again. She comes over last Monday to "..talk" as this is our last chance to see each other before she returns to college 1 1/2 hours away. Similar to our last encounter, we make plans to watch movie / do other things but end up fooling around the entire time. This basically ends with us naked on my bed, pushing the limits of anything she has done sexually to this point. Not fucking of course. She's still a virgin. In our actual talk, she admits she won't actually date someone until she's known them several months (4 or 5). But since then, she now is VERY interested, telling me every day how much she misses me, and how alike we are. This continues to today. I really do like this girl. I would consider dating her in the future. Without a doubt, I want to fuck her. I am very much infatuated. But now she's back at school, and I would only get to see her a couple times a month.

Enter Friday, June 24th. My crazy ex returns to my college town. Keep in mind, until this point her and I have had very little contact, and have agreed to be "friends". She calls me almost as soon as she's in town, invites me to dinner, pays for it, tons of flirting, etc. I hang out with her until about 9, then tell her I have some party to go to without her. The next day, she calls me again, asking to go to lunch, and help her with financial aid stuff and a ride to town. And me, still feeling quite guilty over what I did, oblige. Around 4pm, she is sitting in my apartment smoking up and takes her shirt off. She tells me how she considers me her "gay friend" when the conversation turns sexual. Swearing she won't fuck. I of course tell her the last thing I'd want to do is fuck her again. Well we take an... awkward trip into town with another friend of mine. Coming back, I drop friend off and she's at my place. She lays on my couch and asks me to cuddle with her. Being the sucker I am, I oblige... and half an hour later, she's got my cock in her mouth, and I make her cum when I go down on her. I try to fuck her, and she says "No." flat out. She grabs my cock, putting the tip in, teasing the shit out of me. But that's where it ends.

What a fucking trip. I know for certain I don't want to date my ex again - at least not now - but goddamn she was a great lay. What would be perfect right now? Casual sex with my ex, while keeping the virgin my primary focus. I am fairly confident I should be able to achieve these at the current rate... but I also have a gut feeling that both are dead ends. At times it feels like both are just using me. Ex has stated she has been "talking, to say the least" with her main ex-boyfriend, and is going to visit him for Thanksgiving.

Guys.. what the fuck do I do?

1. Fuck your ex, you already have her. I don't think you will get a chance later.
2. Don't tell virgin about this, when you meet her "Escalate". You guys are not in a relationship, so sleeping around is fine.

Word. I've only told virgin that ex is back in town and trying to get with me. That encounter and future with my ex is our little secret. I debated the ramifications of what virgin might know about ex... the right about of information could probably spark jealousy ploy and pre-selection in my favor. Right now, virgin has quite the ego, and probably believes she can find someone better and closer to her age. I think by hanging out with my ex a lot, and having a secret sexual relationship it will definitely work out well for me.

I would tell the truth if virgin asks questions though. Thanks for the reply.

So I've got a little update. Today, hung out with the ex again. We went at it at my place, and this time when I tried to fuck her she said "my pussy is off limits, you can fuck my ass though" so... fuckin sweet right? Well, I've never fucked her (or anyone!) in the ass before, and I'm doing it for maybe a minute or so when it slips out and I shove it in her pussy by accident. This freaks her out and totally kills the arousal. Afterwards, we have a long conversation talking about past and present relationships with other people. And asks me to keep our "thing" a secret - fine by me. She doesn't want her ex to find out, as he would get extremely jealous. She logically wants to friendzone me (has stated blatantly) but obviously I can still turn her on just fine.

Right now, I'm afraid of putting too much interest into either one. If I read this topic of mine 3 years ago, I would be astounded. I'm quite proud of myself regardless. Having my attention divided is good at preventing one-itis with either, but the psychology aspect of sex with ex is preventing me from keeping my own head in the game. I'd like to be able to fuck my ex in every way possible, but I suppose working back to vaginal sex is going to be a trust issue.

As far as the virgin is concerned...

What's the best way to maintain her interest? How often do I contact her, how often should I push for a meet up, and should it be at her place or mine? She's dorming and has a roomate, so for any realistic escalation I would have to get a hotel room most likely, or to get her to visit me.