Well that ended up being a fun weekend…

Last night I met bi-guy #2 for a bite in my neighborhood. I tend to have an attitude that if I make 2-3 dates in a weekend (last night being a holiday here), only one will pan out. And that’s how it has worked up until now.  I either only have one date or only one date that interests me.

But I guess sometimes people surprise you.  So, bi-guy #2 appealed to me, more from his messages and his background than his appearance. In his photos, he looked like he had a cute smile and kind of sexy eyes…but other than that, he’s not really my type.  Not that he’s unattractive. Just not what I go for. But his background is journalism (when someone can actually make it as a journalist in today’s world, I’m super impressed), and he even has an Emmy to his credit (my second Emmy winner!), and when he talked about what he wanted in terms of a situation, he focused on not wanting to lead someone on when he wasn’t in a place where a relationship made sense, and that he just wanted a mature sexual relationship. And I loved that he had thought about it.  Coordinating schedules was a little tough, but eventually we figured out we could make last night work.

I showed up at the restaurant and he looked exactly how I expected him to look. Which is good and bad. I obviously had decided to go out with him, having a good idea from photos what he looked like, but since he wasn’t 100% my type, I kind of hoped he would be hotter than his photos. But nope.

Dinner conversation was good. He was clearly intelligent. And he was interested in me as a person, not just as someone who might be willing to provide sex without a relationship. I mean, that’s the #1 way to get a date from me – to treat me like a human – and that’s something A LOT of guys can’t seem to manage.  But most still are focused on me sexually, which is fair. I get that. But he was interested in other aspects of me and what I’ve done in my life.  And he was just…a gentleman.  Poised, respectful, complimentary…just a gentleman.

So, after we’d paid up (of course he paid for me, because he’s a gentleman…not required, but nice), he asked if I wanted to go somewhere else. So I took that as a sign he was interested. I had decided at some point in dinner that I liked him and had a good vibe from him.  So, I asked if he wanted to go back to my place.  He was clearly surprised and asked if I was sure… and I said “well, I just asked you, so yes, I am” and he laughed. When we got outside which was a little more private (though still a busy street), he pulled me over to tell me how hot that was that I had just asked.

So, we got to my place and…he may not be the hottest guy I’ve had sex with. He may not have the best body or the best dick…but damn. He had some skills.  It was sort of this interesting thing how he could still manage to be polite and respectful and soooooo dirty (in a good way) sexually.

I will definitely make an effort to see him again (as opposed to having the attitude “if he messages, I’ll go out again…if my schedule allows”) as I think sex with him will just get more fun.  And he seemed very interested…asking my schedule and saying a couple times that we could be in touch while I’m doing some travel and get together when I’m back.

I figured at some point I’d have sex with different guys on back to back days.  But it hadn’t happened yet.  So I was wondering how I’d feel about it. And I really am fine with it.  It’s kind of not even a thing that seems worth contemplating anymore about. I met two nice, interesting, attractive guys who I felt comfortable with.  And had (protected, of course) sex with both of them. And it was fun.  No one was led on, no feelings were played with, no games were played…it was just good fun.



And I mentioned my blog to a guy…

and he thought it was awesome.

No, I didn’t give him the link. Just said it was very anonymous and kind of gave him the overview of topics.  We had met for a drink, sort of last minute (arranged last night/this morning).  I wasn’t excited to go outside. It’s super cold.  But something about this guy made me want to meet him.  He identifies as bi, and that certainly is a draw for me.  I just think it’s kind of hot to think about or see two guys together. I feel like that’s still seen as weird, even though it’s “normal” for guys to like lesbians together.

So we met at a local brewery where I was last Sunday…thankfully he arrived first and grabbed a table, rather than the bar, because it was dead last Sunday, dead tonight, and the same bartender was on duty both nights. I do wonder if bartenders tend to notice me there with different guys…I don’t care much. Just wonder.

So this guy and I had a great time just talking about people, sexual attitudes, experiences, etc. It was comfortable. And funny.  He presented the comfortable guy vibe that I tend to have with gay guys – where I just get a sense of fun and non-judgment.  But, you know, someone who might be interested in having sex with me.

So I invited him back to my place.  And when we kissed, it wasn’t necessarily fireworks. But it was really nice.  And the sex was really good. Again, surprisingly so.  It was different than most of the sex I’ve had lately. He clearly knew what he was doing, but he was ever so slightly hesitant. I don’t know if that was good or bad, but the overall vibe was really nice.  And I think I’ll see him again.  He made sure to get my # before he left (I don’t give my # out before I meet someone).  And I think he could be a fun..uh…friend.

And now tomorrow I am meeting another bi guy.  Hmm…ideas 😉

I guess people have to find a way to stay warm 🙂

I definitely would be happy to stop meeting so many new guys. It’s just not easy to find schedules that align, respect, good sex, etc.  This guy has the potential to work out.  And someone who is just laid back. And not nervous about the situation. Or at least he doesn’t seem to be. We’ll see.

Not who I planned to go out with, but still good…

Before xmas, I started chatting with a guy who seemed really into meeting. I was interested. I can’t say I as blown away. But definitely interested. Schedules didn’t align before he left for a longer holiday break, but he kept in touch over the holidays and we planned to meet last night. He checked in during the week a couple times. I touched based with him Saturday…made sure we were still on. He said he was still into it. Just give him a place and time.  So I did, maybe an hour after that message (I was running errands and my hands were too cold to type as I was walking around).


Sent a message yesterday…nothing…

Now, this is familiar. Guy makes plans to meet and then ghosts. I figure reasons for ghosting include, but are not limited to, decided to go out with someone else, is really a shut-in who gets off on messaging with random photos taken off the internet that are “him”, is in a relationship and never intended to go out…whatever. It happens. I just wish more guys had the decency to do what the guy I was supposed to meet last Sunday did – he texted about 2 hours before we were supposed to meet (after confirming) and said he just wasn’t comfortable and probably wasn’t over his ex, but he just couldn’t meet.  That’s cool. Maybe mildly disappointing, but I appreciate the honesty.

So, around 3pm, a different guy (I’ll call him “Med Student” because, well, he’s a med student) I had been messaging the day before who I had decided I wanted to meet messaged. Asked what I was up to.  I was honest. Said that I wasn’t sure if I had plans or not and was going to give the guy until 4:30.  Med Student was good with this. Made a few jokes about the guy, and said he’d love to meet up if I didn’t go out with the other guy. I appreciated that I could be open about plans and didn’t have to pretend that I wasn’t dating around.  Med Student messaged again about 4:28 and asked how things looked 🙂 I told him that I’d be meeting him if he was still up for it.  He was, so even though my original date ghosted, I could keep the time and place for meeting :p

Med Student was a super nice guy. Smart. Just, really, a good guy.  He had seemed a little edgier in his profile and messaging than he did in person, but we had plenty to talk about.  While I wouldn’t say I was head over heels, I was enjoying myself and there was an easy comfort between us. We left the bar and started to make out outside. But with both of us dressed for the bitter cold, it was more funny than hot.  Too many layers of down…so we went back to my place and, not all that surprisingly, had sex. I wouldn’t say it was mind-blowing, though I could tell by his look of concentration and focus, he was utilizing his anatomy skills.  But it was good.  Probably very good. Definitely room for improvement. But very good.

He had a 5:30 am flight, so had to leave, but seemed very interested in getting together again. And I’m interested in that. I think sex with him was a little less uninhibited as sometimes it can be. And that’s sometimes how sex is.  But I saw signs that he could be very fun.  And, from his perspective, I think I provide a pretty good situation – he’s moving from Chicago in the late spring (presumably) for his residency.  So I can be something casual until he leaves.  And I certainly have no problem with that. And he is a lot more convenient geographically than most of the other options I’ve been exploring. So, we’ll see if he becomes a bit more regular. He’s out of town, and then I’m out of town. So, it may be awhile before we can explore things again. And I’m fine with that.

Accepting Rejection

One of the kind of surprising benefits of this dating with no intention of finding anything serious thing…I’ve learned to accept rejection.  I remember that I used to feel, well, so rejected when I was rejected. I’d kick myself for being too fat, too dorky, not pretty enough, not cool enough…whatever.  It was always something *wrong* with me.

But the thing is, when you have a somewhat discreet profile image up and have to reveal your face later to prospective daters, you have to get over the fear of direct-ish rejection.  Some guys never message back. Some message back saying you’re not their type…And others are wicked excited about the pictures. In other words, not everyone (even me, no surprise) is everyone’s type.

We all obviously know this.  Have a silly conversation with friends and you realize that agreement on celebrity hotness is rarely even possible.  Why should mere mortals be any different.  But yet, at least as a woman, I’ve spent most of my life feeling like something was wrong with me if I was rejected.

Just like the physical, there are also people I click with and people I don’t.  I can’t always say why.  Sure, sometimes there is something tangible.  But often, it’s just about the rhythm of conversation.  And if I’m finding that, why wouldn’t the same be true on the other side of things?

All this is logical, of course. And I’m sure I knew this for some time. But it wasn’t until I went through the sometimes day in/day out rejection cycle (look, a woman saying she is open to casual sex gets A LOT of messages on a dating site) that I really got it.  And sometimes rejection has nothing to do with me! I’ve had guys seemingly blow me off just to message a month or more later saying they were in a bad place and sorry they dropped the ball.

I just wish I could impart this wisdom to a younger me. It would have really saved so much time and energy second-guessing myself.


The reason I started this blog, in large part, is because I think sex is still too off limits for real discussion – what people do, what they desire, what they enjoy…no one talks about! And sex is fun and enjoyable for a lot of people (if someone doesn’t enjoy sex or has no interest, that’s cool too…).  Anyway, I was asked by a friend, who is younger and less experienced, about orgasms during intercourse.  That got me talking to her about the 3 different types of orgasms I know I can have and kind of the mechanics of them for me.  Everyone is obviously different and what works for me may not work for someone else. But I thought I’d put it out there what works for me and, to the extent I have the mechanics really figured out, what those are.  By no means do I think I’m an expert, but I definitely know I know a lot more about achieving orgasm than I did 10 years ago.

Orgasm Type 1 – Clitoral Orgasm: The clit orgasm is probably the easiest for most women to achieve and is probably the most familiar.  As the name implies, clit stimulation is the key to the clitoral orgasm. One thing I only recently learned is that the clitoris isn’t just that little button that (I hope) most of us can identify.  It goes beneath the surface and has a whole lot of nerves going on.  This is a great lesson in clit anatomy: http://projects.huffingtonpost.com/projects/cliteracy/anatomy

So, basically this tells me that there is a whole lot of clit going on and it’s no surprise that some women apparently have very sensitive labia and surrounding areas.  Anyway, I think “self-exploration” (i.e., masturbation) is key to finding out where you like stimulation, how you like stimulation, and what order you like stimulation.  I seem to like a more generalized stimulation that eventually focuses on the button we all think of as the clit.  Sometimes I don’t need much. Sometimes it can take awhile (like 20 minutes or more).  The clit orgasm, to me, is that familiar, leg-twitching, intense building feeling.  Sometimes I can’t take it continuing because it’s too intense, though backing off slightly and keeping it going can lead to even more pleasure.

Orgasm 2 – G-Spot Orgasm: I’m not here to debate the existence of the g-spot and I have no idea if everyone has it.  I seem to have a spot on the front of my vagina, maybe half a finger length in (so not far) that is sort of raised and rougher than the rest of my vagina wall.  I had one fabulous partner really walk me through it.  So, he showed me that if he put pressure on it when I was aroused (he did that “come here” finger movement), it kind of felt like I needed to pee.  Rather than clenching up, trying to hold it, he told me to do the opposite kegel – as I was feeling that pee sensation, I should think about opening up.  Well, as soon as I did that, I squirted all over him.  Now, I think squirting is hotter for the partner than it is for me. It’s kind of cool. And it is a release.  But it doesn’t quite have the same type of pleasure as the other two orgasms. Since my increased awareness of this type of orgasm, I’ve found a lot of penetrative sex more enjoyable.  When I start to feel that kind of tickly, “do I need to pee” feeling, I let go and open up instead of clenching up and things feel so much better.  Sometimes I squirt. Sometimes I don’t.  But it definitely increases pleasure.

Orgasm 3 – Dual Orgasm: I call it the dual orgasm because the clit and g-spot are both involved.  I first discovered this one with a partner who used lube and digitally stimulated my clit while I was on top.  And it was…intense. With this type of orgasm, I kind of feel like I’m going to pass out in the most intensively, enjoyable way possible.  For me personally, I tend to have these types of orgasms most often while on top.  Sometimes doggy style.  And it’s also possible if clit stimulation is added to really intense fingering of my g-spot.  I haven’t yet experienced this type of orgasms in any position with the guy on top. I’m going to guess that’s because in that position, his dick is pressing against the back side of my vagina more than the front.  But possibly with a large enough dick, I’ll be able to get there.

So, there may be more types of orgasms that are totally different than these (I’ve seen a 4th type listed as multiple orgasms…but I don’t see that being of a different kind than these. These truly feel like just different kinds of orgasms to me).  I’ve heard some women can have orgasms through anal stimulation alone.  I haven’t found that, though it can add to any of these others and increase the pleasure.  I also wonder if I can ever get to the point of just thinking my way to an orgasm – I had a friend once who claimed to be able to do that. So, that’s saying this list is by no means definite. And the logistics are specific to me.

The number

Lately I’ve been thinking about what “the number” means.  I’ve been asked a few times what my number is.  And my honest answer is, I don’t know.  Let’s start by defining what the number consists of. Is it just penis in vagina episodes, no matter how brief? Is it more substantive penis in vagina? Is it oral? Is it mutual masturbation?  Anal?  It seems a bit silly to me to count a time where a guy put a condom on, put his dick in me, couldn’t keep an erection, and it was very unsatisfying all around…but not count sometime that involved very kinky, dirty, and very satisfying licking, sucking, fingering, etc.

So, that’s my first issue with “the number” – it just is an undefined way of keeping track that is somewhat misleading.

But even if I did decide on a way of keeping track, what is the point of “the number”.  Yes, I understand that, in theory, the more people one sleeps with, the higher chance of an STI or STD.  But that is certainly offset by safe sex practices and regular testing.  Since there is never any guarantee that one’s partner has been honest and monogamous, it’s pretty tough to say what is safe and what isn’t when it comes to sex (unless one totally abstains).

So, as my number creeps up (no matter how one counts), I keep wondering if it matters.  Society certainly tells me it does.  But do I care? I’m more fulfilled with my number going up than my number stagnate b/c I’m celibate.  And while I recognize that there is, in a perfect world, an in between of landing on a some casual partners and sticking with just who I’ve decided to go with, it’s not necessarily super easy to find casual partners with the right attitude, chemistry, and availability.

So, for now, I’m not worrying about my number. I don’t actually know what my number is (but know enough to know that n+1 is greater than n). Maybe I’ll care at some point. Or maybe not.

Is the conversation with a 26 yr old supposed to be better than the sex?

Last night I met another 26 yr old.  I started messaging him because he looked to be my type and we had a few things in common based on his profile.  In messaging more, it seemed like we had more and more in common, plus the potential for good sexual compatibility.  So we met last night at a bar that usually has a relatively low key crowd. Unfortunately it was a stop on a bar/beer tour of Chicago at the time we were meeting and fight songs galore were breaking out (very odd at a bar that has an older punk vibe, if that makes sense).

He was really really hot. Man was he hot. Damn.  When I first walked in, I got a look that I wasn’t sure how to interpret, so I was somewhat self-conscious.  But quickly we were chatting away about various substantive things…including our mutual love for the same modern philosopher.  It was a very good vibe and after a drink, went back to my place.  I showed him around and when he kissed me, well, he was a fantastic kisser.  Unfortunately the sex was just…fine.  I think he really enjoyed it.  But I suspect he was a little more nervous than he let on and rushed things a bit. Normally, I’d sort of feel like “ok, lesson learned. He’s 26. I don’t feel like being the training ground if he hasn’t had that already”.  But…he was a super cool guy.  (And did I mention that he’s so hot???)

We ended up hanging out for about 4 hours, probably having sex/making out a total of 30-45 minutes of that. The rest of the time, just talking about dumb stuff, interesting stuff, all kinds of stuff…and it was easy.  Definitely didn’t expect that from a 26 yr old.

So, I’d like to see him again. Maybe I am willing to do a little training…he doesn’t want anything serious.  And he’s off on vacation soon and then I’m out of town, so it could be awhile before I see him. But there aren’t many guys I can discuss social justice with AND enjoy naked…Last night I was wishing for a weird time machine where a younger me could meet him in a few years. He’s totally my type of guy…except definitely not remotely in the same place in life. That, more than the age, is why he’s too young.  I can’t complain about the conversation. And, hey, he really is hot.