Since I brought up online dating… 

It seems like I’m noticing more of the ridiculous. These don’t bother me, but people are so clueless.

First, no… That quite literally is a car (I mention that I don’t understand why all the car pics in profiles and they seem like men are compensating). And this guy is quite outside my age range. And eww. 

Second, it’s quite possible (and actually, true story, is the case) that I’m both a real person and find you uninteresting and unattractive (and I still haven’t figured or why it shows me always online, but I figure it’s an app setting I haven’t figured out)


Shockingly (sarcasm), this initial message did not entice me

While I appreciate the concern about STDs, and am all for asking about them, maybe engage me first. Problem # 1. #2 is that he assumes this is only about his pleasure. # 3 is telling me what to do. #4 assumes he is the only one who gets to choose whether he’s  interested. #5 is that he is outside my specified age range and assumes I’m fine with that. I’m not. #6 “your”

What’s too young?

When I was working out yesterday, I realized that if I added the ages together of the 2 guys I had sex with last week, their combined age was only about 9 years older than me…closer than I am to either of them. I’m fine with that. I have a few friends who have husbands 15-20 years older and that seems like no big deal…but I don’t know anyone with the situation flipped.

I find younger guys are more respectful of me. Maybe because we’re at different points in life, there is less competition. And younger guys tend to be kinkier, more open-minded, more into casual…it just works for me. I didn’t expect that to be the case, and had NO idea that all these younger guys were into older women.  I look at pics of myself from my 20s and while I was certainly hotter (IMO), I didn’t have the confidence I do now. So I get it. It’s just a little weird when I see a guy and know that the last woman he slept with was close to 20 years younger than me…am I in competition with these women? I don’t want to be.

So what’s too young? I have sort of arbitrarily set the age at 24, though I haven’t hooked up with anyone younger than 26. My thinking has been that the brain is fully developed around 24, so I’m not taking advantage of someone improperly. But one male podcaster in his late 20s who I listen to thinks that all women over 45 (not there yet) should fuck a college-age person at some point to show them how to have good sex…It makes sense to me. But I haven’t done that and don’t know that I could. So I don’t know what is too young. And I don’t know that I could get into a guy younger than 25/26…but I never thought a 26 yr old would actually be more than a fuck buddy to me and, well, Trump Hat Guy has made me question that. So I don’t know what is too young if a guy seemed mature (I mean, obviously someone would be a legal adult, that’s a given. I mean beyond that).

Finally pegged Trump Hat Guy!

Or, well, anyone…I lost my pegging virginity.  So, when THG and I first were talking, pegging came up. So it’s been on the table, but just circumstances didn’t work out. It seemed like a lot of potential awkwardness to take on the first time we had sex, and other times I’ve just gotten caught up in other stuff or been too tired.  But I still wanted to do it and he wanted it. So yesterday I texted asking what he was up to this weekend and we ended up talking about getting together last night. I asked him if he wanted me to fuck him with my strap on and I could tell immediate interest on his end.

In the few hours before he came over, I could tell I was nervous, and I wasn’t sure why.  THG and I have an easy vibe and I wasn’t really worried that things would go badly, but I could tell that I was on edge. But when he showed up, it went away. He had some kind of eye issue going on (I actually truly hope he’s ok…he’s getting it checked out now) and didn’t have eye drops (I did) and had actually never put eye drops (or contact lenses) in his own eyes and was nervous. So I told him that I’d put them in him…which he did comment was a little motherly and weird, but he was desperate. And with all my pets and foster cats, I figured if I just pretended he was a pet, I could do it. So our evening of pegging started with him lying on my couch while I pinned him down to put eye drops in his eyes…(it apparently helped a little, but didn’t solve the problem, unfortunately).

But that did lead to making out on my couch and we went upstairs where I proceeded to take control – which I normally don’t do, but I don’t mind with him.  I got him naked and went down on him a bit. I didn’t know if he was going to let me stop to go put the strap on on, but I shouldn’t have worried.  When I got it on, he immediately started sucking the (very lifelike) dildo, which I found incredibly hot.  Finally I made him get on all fours…we had to do some adjusting b/c he’s fairly tall, but eventually we got a position where I could start getting him ready…I was surprised how little warm up he took (tonguing and fingering) to be ready for the dildo.  Indeed, I was surprised that I actually could have gone quite a bit larger (and I’m going to have to, next time). The thing about pegging from my perspective…it’s all about the idea and the visual.  I mean, I can’t feel it since, quite obviously, the dildo isn’t my own body. But I did find it really hot to be in charge of his pleasure. Eventually he wanted me to stop so he could take care of me, but I wouldn’t let him, which was also kind of fun.  To just be in charge of when I would stop.  Finally I decided it was time and replaced the dildo with a rather large butt plug (that he easily took).  His intent was to fuck my ass, but we just couldn’t get the logistics down. I don’t know why, but it wasn’t working and I really wanted him at this point. He was nervous about regular sex b/c he’s one of those guys grossed out by periods. But since I use the Instead Soft Cup (yes, a shout out to them), I assured him he didn’t have to worry about blood and it was all blocked. Either he believed me or didn’t care at that point and he started fucking me and oh my god…it was sooo good. I don’t know if it was because it had been awhile since I had had period sex or if it was just being turned on by this point from the pegging, but it was amazing…

I’ve mentioned before the different types of orgasms I have, and somehow with our position, I went from a g-spot only orgasm to a full on dual intense orgasm that I totally didn’t see coming and we somehow managed the most simultaneous of orgasms I think I’ve ever experienced. We were 100% in synch and it actually kind of weirded me out a little how much we peaked simultaneously.

After we both kind of caught our breath, he went in the bathroom to check on his eye and said “you’re right – there really is no blood!” So hopefully we don’t have to have this discussion next time I have my period because I really do have annoying long periods that come more than I’d like.

We hung out the rest of the night – ordered some food and while we were waiting, talked awhile and then he fell asleep on my chest as we were cuddling, which I found kind of sweet. After we ate and decided to go to bed, said when we got in bed that he did feel like I actually care about him, and that means a lot because he doesn’t have a lot of people he knew in our city who care about him (he’s relatively new to the city, although he grew up in the general area) and that he liked just eating together and hanging out. I think I have known that he consciously thinks about his image to the wider world, but doesn’t really believe many people know him, but this was a reminder of that. I genuinely think he’s a good person (despite his presidential preferences) and I truly feel respected and appreciated by him. It’s just easy to be around him. And this time, I actually fell asleep in a normal amount of time for me and slept very restfully. When we woke up and his eye was still bothering him, we talked for awhile about where he should go and what he should do and I helped him find an option (waiting to hear from him tho). And I didn’t mind that he was taking up my morning and my day wouldn’t go as I prefer it to go. I guess I like him. Of course, it helps that he finds it hot to hear about me with other guys, so even though I like him, I don’t have to change much (if anything) about my life to have him in it. And whatever happens with him, it’s a good reminder of what it feels like to have that comfort with someone who isn’t just a platonic friend. Who I feel like I can be myself around and it’s not something he puts up with, but it’s what he likes about me.

But….I will admit when I was fucking him in the ass, I did remember that he likes Trump and took a little bit of joy in fucking a Trump supporter in the ass 😉

When the world of a big city is too small

I live in a big city. I’ll leave it at that. It’s big. It has real public transportation. I have literally never randomly run into basically any of my friends at a place where it wasn’t likely they were going to be. This has to be understood for this next part.

So the comedian I referenced awhile back (maybe at some point I’ll link) had started things up with me through Facebook. So we’re FB friends. Since our hookup, we talked about getting together once awhile back, a long while back, and it didn’t happen. And that’s totally fine b/c I’ve really only remained FB friends with him to hatewatch his FB page. He’s kind of jumped the alt-right shark…for awhile, I thought it was a targeted commentary on the alt-left hypocrisy and now I think he’s full on drunk the kool-aid. A month or two ago, he posted something intentionally inflammatory. Since he has a bunch of liberal friends, they were arguing and I noticed one asshole chiming in with just completely misogynistic, stupid, and bigoted crap. I don’t know why, but I clicked on his profile.

And he was this guy.   I scrolled through all the public pics to make sure it really was the same guy. It definitely was (ok, I didn’t get his last name at the time, just his first, and frankly I had forgotten it).  And I’ve noticed he brags all the time about how amazing he is at sex. And frankly, he was just fine. I mean, he had followed up once or twice about getting together again and I decided that really, in retrospect, he wasn’t worth the effort (and he smelled too much of wayyyy too much smoking).  So now he ruins the hate watching of the comedian’s FB page b/c he’s always talking about “laying pipe” or whatever.

I *assume* they don’t know they both had sex with me (since I’m close to 10 years older than both of them, I would imagine they wouldn’t even guess our paths would cross), but who knows. And it really doesn’t matter. Neither of them have tried anything creepy through FB, so I don’t think either are terrible people in the one on one sense. But every time his dumbass comments pop up in my feed I just have to shake my head that the world is too small sometimes.

Is online dating *that* bad?

Last week someone messaged me on an online dating site and asked me how often I’m harassed.  And today I saw a Facebook thread bemoaning the harassment in online dating.

But, here’s the thing…I get probably between 20-200 messages a week online (I should count some week. I haven’t). And so far, I’d say the number of problematic men has been well under 1%. Probably .01%. I don’t know. Five guys come to mind and one of them might have just been clueless. Of course, I just delete the unwanted dick pics and the “hey baby, can you handle my 9 inches?” messages. So even if I included those, I would say it is less than 1-2% of the total messages I receive. I have been solicited for sex work 2-3 times (again, total…that’s in 1 1/2 years of my primary, sexually forward profile).

So am I lucky? Is it my age? Or is it that people hear how bad online dating is and want a horror story? So far, for dates I’ve gone on, I have 3 bad dates. 2 dealt with political assholes (if you don’t like that I’m voting for Hillary, STFU and don’t tell me that her vagina is her only accomplishment) and 1 that seemed ok at the time, but I rejected, and now he periodically sends me innocuous, but unwanted, messages thru the dating site (and he’s one I would put into the problematic category).  The others? at worst they’ve been dull.

Obviously I’m an experiment of one and I don’t want to suggest there aren’t problems. But I do have to wonder what the real story is.

Edit: And I’ve already been attacked on the Facebook thread for suggesting that maybe we do need to look at issues in society about how women treat sex as something they give away and men treat it as something to hunt down…if everyone could be more honest about their desires (or lack thereof), we might see some improvement. I really don’t understand why talking about broader societal influence is problematic. I was careful to say that no one should be harassed, etc. But if we throw our hands up and just say “all men are stupid” without actually trying to see why we are in this place, we have no solutions. Which makes me wonder how much of the complaining is just complaining for the sake of complaining and how much represents actual problems.

Ahhhh. yes. that was good. very good

I had a boring weekend. Sort of by plan, sort of by happenstance. I needed it. I wanted it. But I also was feeling like I really wanted some nice pleasure. But I didn’t feel like meeting someone new and I didn’t really feel like trying to line things up with someone “old”.  So basically, I didn’t do anything. But yesterday on my run I was thinking about Superman. Wondering what he’d been up to. Hoping I’d get to see him soon. And vowing to text when I got home.  Which I promptly forgot about b/c I find that what I think about during runs leaves me as soon as I finish the run.

And then a few hours later, “Hey. How’s it going?” from Superman…did he know I was thinking about him naked? Probably…so I told him I’d been thinking about him. Turns out he obv was thinking about me.  We make plans to meet next weekend, but I said to let me know if he’s ever in my ‘hood b/c you never know if our schedules would line up. He pointed out he gets off mid-afternoon. I said, “well, for example, tomorrow I have a call at 6:30am, so I’m just going to work from home.”  This morning he texts asking me if he wants me to swing by when he’s done. Um. YES. Please god yes.

It took a little scheduling to pull it off, but he got to my place late afternoon.  The thing about our energy is that we’re kind of friendly/pals, both a little awkward and slightly shy, then we get naked and just know how to touch each other and lick each other. Or he does me. And I am pretty sure it’s mutual. So we’re chatting, he gets in the shower, I go and give my dogs chew treats (seriously, they have been sooo annoying since I got the new cat. They don’t like that she sits outside my door with them and that makes them barky. gah. I need a solution b/c the chew treat only lasted for 10 min or so).  I join Superman in the shower and he starts touching me and…fuck yes. It’s on. After some light shower oral, we get out and he just buries his face in me and I can’t remember the last time I truly fully and totally came during oral, but I did. For soooooo long.  Then he starts fingering me and I start soaking my bed.  And I feel like I’ve had countless orgasms as a warm up.  He was so close to coming that I don’t even think I gave my best effort for a blow job before he came.  And he was immediately hard right after because, you know, he’s 27. And I guess 27 year old guys can do that. So I climb on top and it’s just ok, a little awkward and then, omg. He finds the spot.  And I just start this endless orgasm that soaks the bed. By the time he climbs behind me, I’m pretty much toast, but I was able to keep low grade coming until he came again.

And then, like a good FWB, he got dressed to leave. Don’t get me wrong, some FWBs are great for conversation. He’s not one of them. He is soooo sweet. And doesn’t have a mean bone in his body. And he is hot AF IMO. But our conversations are kind of shallow and I’m fine with that. He is almost the perfect FWB. The sex is top notch. He’s nothing but respectful and sweet and easy. And I don’t have to worry about real feelings for him. If he met someone and disappeared with her, I’d be genuinely happy for him. And if we keep up an every month to 6 months fucking schedule for the next 10 years, I’d also be thrilled.