Entries categorized as ‘CB (aka Chicago Boy)’
I must say, R- is a pretty cool guy. He’s been ringing me up to go out lately and every time he does, I’m with NG so haven’t been able to chat. I finally e-mailed him with an update on my dating scene and told him it would still be fun to catch up over drinks. He responded enthusiastically and said he wants to hear all about NG. That is pretty cool. I like that we can be friends without the sex component.
I injured myself snowshoeing (I know, how the heck do you hurt yourself snowshoeing?) with NG a while back and ended up chatting with CB about it online. He offered some helpful advice on how to ice it properly. I had wished him a happy belated birthday on his myspace page so he pinged me to say thanks. Apparently, everything is “going really great” in his life. Pardon me for a moment while I sarcastically jump for joy. It’s not that I don’t want him to be happy, it’s more that he doesn’t seem remotely interested in whether I’m happy. He didn’t ask anything about how my life is going. A little give and take would be cool. That happened a few weeks ago. Such a waste of 5 minutes. Narcissistic rock star wannabes. Gotta love ‘em.
10 days until NG returns. Not that I’m obsessing over it or anything…
Categories: CB (aka Chicago Boy) · R- (a lover)
Tagged: CB (aka Chicago Boy), Online Dating, portland dating, relationhips
It’s funny, I don’t have a whole heck of a lot to say about NG at the moment. Everything is going along really smoothly. I don’t have any drama, the sex is incredible, and I’m totally cool with the amount and quality of time we’re spending together. I suppose the only weird thing is my general reluctance to call him my boyfriend. The occasion to do so hasn’t come up yet, and I think when it does, that’s what I’ll say. That he’s my boyfriend. I think it’s because I’m not accustomed to having boyfriends back-to-back like this. He hasn’t referred to me as his girlfriend in my hearing, not that there’s been any cause for it on his end either.
Speaking of back-to-back boyfriends, CB pinged me via IM the other day while I was out with NG. It was a “hey, how’s it going?” sort of thing. I didn’t see him online for a couple of days after that and when I responded with a “good, how are you?” he didn’t say anything. Maybe he only contacts me when he’s had a few. It was, after all, after midnight. If that’s the case, it’s pretty lame.
Categories: CB (aka Chicago Boy) · NG (aka New Guy)
Tagged: Dating, Portland, relationships, Sex
In spite of still being sore from our previous sexual marathon, I went for it again with NG last night. I couldn’t help it. He is really quite spectacular. No sex tonight though. I’m contemplating using a dildo made of ice. I’m not sure how I would accomplish such a thing but it sure sounds nice. Perhaps I will sit on my couch with a sack of frozen peas in my lap. That’s a good way to spend a Friday night, no? I’m hoping for vast improvements on Saturday.
On a side note, CB did end up returning my last text from the morning following his drunken texting. He said in response to my well wishes regarding his probable hangover, “Sleepy.” I didn’t respond and he hasn’t said a word since.
Getting back to NG (who is the one who counts now) we had a really great time hanging out last night and we spent all day together today on a mountain adventure. You’ve just got to love Oregon’s late winter snow storms! When we got back we curled up on the couch together in a sort of semi-horizontal hug configuration and made each other laugh while we talked about silly things and basically marveled at how excited we were to have met. It’s pretty neat. The interesting thing is that I feel very comfortable around him because he seems so laid back. I also feel like my head is still screwed on straight, which is cool. Here’s to hoping!
Categories: CB (aka Chicago Boy) · NG (aka New Guy) · Sex · Wellness
Tagged: Dating, Online Dating, Portland, relationships, Sex
I got my first drunken text last night from CB. Dude totally woke me up at 1am to tell me he was sending me a drunken text. Then he asked me to meet him for drinks. I declined and explained that I was actually sleeping. At 2:20am he texted me again to ask if I was still up. Since I had just finally fallen asleep again and was never “up” in the first place, I ignored him. I knew the bars were closed and the last thing I wanted was a drunk ex-boyfriend on my front porch in the middle of the night. He was always a giggly, happy drunk, but still. I was in no humor to deal with whatever was going through his head.
I texted him this morning and told him that I’m up now and hoping his hangover isn’t too bad. I’ve had no word in response and I suspect I won’t hear anything from him anytime soon. I suppose it’s nice to know he was thinking of me. But, I have a date with NG tonight and I find myself thinking about him a lot more than I think about CB. Thank goodness!
Categories: CB (aka Chicago Boy)
Tagged: Dating, Online Dating, Portland, relationships, Sex
I decided to update my online dating profile. I was cruising the ads and found that CB is on there again. It felt like a kick in the gut, another nail in a coffin already buried six feet deep. Yuck. FWB has been active on there the entire time I’ve known him, which is totally cool with me.
So, to combat that sick feeling in my stomach, I decided to reactivate my account and update a few things. I don’t know if there’s anyone particularly interesting out there, but I figure, what the heck. It’s always been fun and I don’t see why CB should ruin it for me. Grrrr. I still wish I’d never met him and I really, really wish he’d get out of my head. I should watch Eternal Sunshine of the Spotless Mind again sometime. Maybe it would be cathartic.
Categories: CB (aka Chicago Boy) · Online Dating · Portland
Tagged: Online Dating, Portland, Sex
February 19, 2008 · 1 Comment
My goodness, where to start? CB and I broke up a little over two weeks ago. The problem with our sex life never improved and in fact seemed to get worse as time went on. My take on it was to be really positive, and let him know that we could try as often as he wanted. My fear that he would start to lose interest in sex came true. We pretty much only had sex when he felt like he would most likely orgasm. When he didn’t orgasm, his frustration was palpable and made me feel unfulfilled, even if I had orgasmed. I felt like there was some button I needed to push to get him over the edge, but I couldn’t figure out what it was.
The course of our relationship went something like this. We met. We fell in love. He’d never felt this way about anyone before. He liked sharing his space with me, unlike other girls he’d dated. He’d finally met the right girl. He loved me. And then, cue the doom music (dum, dum, duuuum). Relationships were hard for him. He was scared and confused. He didn’t want to push me away. He asked me to be patient with him. He pushed me away, then pulled me close, then pushed me away. I kept my shields down, knowing we were doomed if I didn’t. He didn’t know if he wanted to break up or declare his love for me to the world. He opted to break up. I was a great girl whom he liked to hang out with sometimes but that was all there was to it. He just wasn’t as into it as I was. He hoped he hadn’t lead me on. I told him I felt like none of it had been real. He was offended and said he meant everything he’d said. If that’s true, then my only conclusion is that he needs therapy. Now.
During all of this, he would make little comments about proposing or getting married. They were comments like, “Wow, if you did such and such, I would propose on the spot” or “Damn, if you really think that’s funny, I should propose right now” and “If you’ve mastered making lasagna, I’ll marry you.” They were all conditional phrases that were entirely within my power to fulfill. Did I do any of them? No, I did not.
I’m not actually in a hurry to get married and he was having such a hard time being my boyfriend, that making him my husband seemed completely ludicrous. Given how freaked out he was about being in a relationship, I tried hard to make him feel safe, comfortable, not pressured. Maddening. Every time I had to be patient, I invested a little more of myself in our relationship. My pride, my heart. It was all for nothing. By the end, his fear had choked the life out of whatever feelings he had for me in the beginning. I don’t know if the doubts I expressed in the beginning about who exactly he saw when he looked at me were true or not. I don’t feel like that’s the case. His overriding fear is the only thing that feels real to me.
I’ve never dated someone and come out of it wishing we’d never met. There’s always been something of value in my relationships, however long or short they may be. But with this one, I just don’t see it. What’s to be learned? Don’t give my heart to a neurotic dick? Duh.
He sees no connection between his inability to orgasm and his intense fear of relationship intimacy. It seems like a no-brainer to me. As his fear increased so did his difficulty with sex. By the end he was feeling entirely demoralized about sex and I had reached the point where it seemed like maybe we should lay off sex entirely for awhile. This is how willing to work it out I was. Sex is a big deal for me and I was willing to put it on hold if it made him feel better.
The day after I suggested we maybe shouldn’t have sex for awhile, to take the pressure off, he called with the news that he wasn’t sure what to do about us, break up or declare his love for me to the world. Two days after that, he decided I was just someone nice to hang out with, as I mentioned earlier.
It took me almost two weeks to get it through my head that it was actually over and that it all essentially meant nothing. That in the end, I meant nothing to him. It left me reeling and I don’t like it. I don’t like that I love someone who not only doesn’t love me back, but who made me feel like a fool. I feel like I’m in the middle of a stupid 80’s power ballad video! In retrospect, I wish I had fulfilled his little conditions for marriage, just to see how he’d react. There would certainly not have been anything to lose!
Since things with CB were for sure over (I sent him a text to verify it, just in case), I spent a lovely Saturday with FWB last weekend. It was easy and fun and just what the love doctor ordered. 
Categories: CB (aka Chicago Boy) · Dating · Portland · Sex
Tagged: Dating, Portland
I’ve been with CB for three weeks and it’s going incredibly well. Hence, my lack of blog updating! I just haven’t had the time to sit down and write about it. I also feel a little weird writing about someone I’m falling in love with. He doesn’t know I have this blog and it makes me feel a little guilty. After this post, I may feel a lot guiltier because I’m about to think through some things. You dear reader, get to be my sounding board.
CB and I are having lots of sex. He totally turns me on and I clearly turn him on. Sounds great, yes? Sadly, there’s a “but…” coming. He rarely orgasms. To make it worse, he’s frustrated by it. We have fun, engaging, raucous sex until I’ve climaxed several times and he’s too tired to continue. He’s in extremely good physical condition so it’s not that kind of tired. It’s more that we keep going until he’s frustrated. It’s all fun and games until the boy can’t come.
His take on it is that we’ll figure it out, we’re having a great time having sex anyway, and being with someone he loves is way more important to him (since finding sex is not difficult for either of us). My concern is that his growing frustration will make him stop wanting to have sex with me and that things will go downhill from there.
I can have sex for a rather long time it seems. Sex with someone I like just flat out feels great, whether I orgasm or not. I’m perfectly happy to keep going until my partner gets off. My last boyfriend (not lover) loved that it took him forever to come with me. He seemed to see it as an amazing bonus. The sound of my voice over the phone was enough to make him hard. His body associated me with great sex. It was awesome. He would sort of get lost in fucking me. It was incredibly sensual and he made me feel like a sex goddess. I guess my point is that it took him an unusually long time to orgasm with me, but he loved it.
I mentioned awhile back that M- eventually told me that not orgasming wasn’t normal for him and he didn’t feel connected to me sexually. He’s a little different though because he didn’t keep his erections once he was inside me, which led to lots of finger banging (which is no longer allowed). I could turn him on easily enough but couldn’t keep him there.
R- would pretty much keep going until I told him to let go and come. FWB definitely held out for quite awhile before he came and it seemed like it took an effort of concentration to reach that point. J- for the most part just came whenever and I never had to worry about it. Of course, that was before M- and I didn’t realize there could be a problem.
I don’t know what it is about me that is preventing these guys from climaxing as they’re accustomed to. I’ve never had children and I haven’t heard any feedback that they can’t feel me. I’m tight, and when I’m turned on I’m also damned wet. I’m enthusiastic about sex, meaning I’m an active participant. I’ll do just about anything short of standing on my head, but I definitely take the more passive role of letting the guy call the shots.
M- said the best sex we ever had was the time I totally took control and had my way with him. I’m not sure I’ve really tried that with CB. I sort of did this morning when I rode the hell out of him with no regard for getting myself off, but rather stayed in a position over him that maximized the feeling and rhythm of my pussy sliding up and down his cock. I got him close, but no cigar and then he flipped me onto my back and fucked me until I came.
Arrrggghhh! He decided this morning that we need to try sex in various other spots around the house. I’m totally down with that. I will try anything at this point. Maybe he needs to accept that sex with me is going to be a picnic in the park instead of a burger at the drive-thru and if he stops worrying about it, he’ll get there eventually. Otherwise, I’m open to suggestions…
Categories: CB (aka Chicago Boy) · Dating · Sex
Tagged: Dating, Sex
I met CB-’s family Sunday night. They were really cool. We ate Thai food and watched game 7 of the ALCS (baseball). He hadn’t brought anyone home to meet the family in almost 2 years so it was kind of a big deal. He met my ex and his girlfriend earlier in the day, which is the equivalent to meeting my family. I don’t plan to ever actually introduce him to my parents. Certainly not my mother anyway!
Tonight, I will watch him play the drums, then I will lick the sweat from his ears before he fucks me silly. That’s my general plan. We haven’t actually had sex yet so I don’t know for sure that he’ll fuck me silly. We’ve messed around enough for me to know that it’s likely though. It’s pretty much all I’ve been thinking about all day.
It’s weird to be this into someone. I keep finding myself wanting to say long-term things but then I stop myself. He doesn’t seem to stop himself much though so, I suppose I shouldn’t either. There’s a part of me that doesn’t quite believe he really wants to be with me. That once he gets to know me better he’ll think, “Oh. She’s not who I thought she was” and he’ll leave. It’s not that I don’t know what he sees in me, it’s more that I don’t know who he sees when he looks at me. There’s a difference. I’m trying to make sure my shields are down so he doesn’t see a blank slate. People project onto my blank slate shields the person they want me to be. It’s pretty handy sometimes, like in a job interview, but it’s not so great when I want a genuine relationship with someone.
Fortunately, I feel very comfortable around him and the doubts only plague me when we’re apart. I certainly feel more relaxed and at home with him than with anyone in a long time. Trust built over time will ease the doubts and in the meantime, this will certainly be an adventure!
Categories: CB (aka Chicago Boy) · Dating · Sex
I am completely sprung on CB-. I actually took down my profile online yesterday and am prepping for the “I’ve met someone” speeches to R- and FWB. I can’t even believe it. We were sitting over dinner the other night and CB- said something that suggested he didn’t want to see anyone else so I said, “<ahehm>Does that mean you want to date exclusively?” my voice rising a full octave by the end with restrained excitement. To which he responded, “I have no interest in seeing anyone but you.” “Neither do I” I said, “In fact, the morning after our first date I realized I didn’t want to see anyone else.”
This was followed by an amusing exchange in which we tried to determine who amongst the people we’d recently dated needed to get a phone call. Anyway, I’m just completely flabbergasted. I had no idea that one person, in a mere couple of days, could so completely sweep me off my feet. Actually, he swept me off my feet the first night and it’s just getting better every day as I start to believe it’s really happening. I woke up this morning missing his sleepy morning face and wishing I could kiss his lightly freckled nose. It’s sort of disgusting.
I checked a minute ago, and his profile is offline as well. Hooray!
Categories: CB (aka Chicago Boy) · Dating · Portland
Tagged: Online Dating, Portland
<ping, ping, ping> Hello? Is this thing on?
Oh my freaking howdy doody! I hardly even know how to describe last night. Fireworks? Big exploding fireworks of “I can’t believe how great this guy is!” I haven’t been on a first date like that since I was 19. We talked on the phone the other day and I just had a really good feeling about him. So far, so spectacular!
The date started off in a fairly standard way except that I let him come to my house first, which I don’t always do. We had a drink and looked at some photos online from a trip he took last summer. Then we went out and shot pool. No big deal right? It’s amazing how different the same date activities can be with different people. I hang out with guys over drinks and pool all the time. None of them are this hot, funny, nice, and sweet all at the same time.
We ended up kissing in the pool hall of all places. No major making out, just a couple of sweet kisses. We talked and laughed and played pool like we already knew each other. I still played like crap though because I was entirely too distracted by his hotness.
The kissing in the car intensified significantly. God he smelled good. I was completely giddy. It’s a good thing I didn’t have to drive because I could hardly see straight. Every once in a while he would let out this happy sounding laugh. Wondering what he was thinking I said, “what?” and he said that he had a feeling he would like me but that he was not expecting to like me so much and that he was really excited about it. It’s scary how much I like this guy already. We hung out for a total of about six hours. To quote him as he left, “Is six hours enough to totally fall for someone?”
Maybe he’s too good to be true but I’m going to enjoy every minute of this. I don’t want to live in fear of being hurt. I think there’s a reason it’s called “falling.” It’s a risk and you have no idea what’s at the bottom. That’s all I can say for now. My head is spinning…
Categories: CB (aka Chicago Boy) · Dating · Portland
Tagged: Dating, Online Dating, Portland