GAHHH…Dumb emotions again

After the 3some on Tuesday, I reached out to Trump Hat Guy to see if he’s still interested in an MMF with hot bi guy at some point.  He wanted to hear all about the 3some and asked if I would let him be my main guy while I continued to sleep with other guys.  I kind of hesitated…I’m not looking for a relationship after all…and asked if the thought of me “cheating” on him was exciting to him. He said that was exactly right. My response was that I was open, but we need to do a better job about being honest with each other. I’m not into being jerked around.  So we made plans to see each other last night…

I had mixed feelings most of the day – excitement about hanging out with him for more than an hour, but kind of keeping my expectations in check in case he flaked on me again.  And when he didn’t respond to my email about whether we were still on for a few hours, that was only  magnified.

Finally he started responding – that he was still at work (I got out early) and was hoping to leave soon.  He didn’t end up leaving until 6 or so, and came straight to my place.  And it was just a really nice night. We ordered food, had sex on my couch, cuddled…he talked to me about some of the not so great parts of his family life and career.  And also how he knows he’s terrible at communication and it has screwed up all his relationships and he really is trying harder with me than he ever does.

And then he stayed over. For me, the most intimate thing I can do with a person is sleep with them.  I almost never do it and it’s not unusual for me to start having a panic-type attack about sleeping over.  But with him, I just fell asleep…it was the two of us, my two dogs, and at least 2 of my cats in bed.  It was cramped and I was completely relaxed.

When I woke up, I walked my dogs and came back and woke him up and we talked a bit. Then I made us breakfast before I had to head to puppy training class…

So it was the most relationship-y night I’ve had in years. There is this thing between us that I wish wasn’t there, but is. My pets flock to him when he arrives and I feel like he listens to me and kind of gets me. The age difference, the political (HUGE) differences (although he is socially liberal), and the frustrations about his shitty communication skills all kind of go away when we’re hanging out. At some point this is going to turn into a thing. Whether it does soon or if we’re still months away, I don’t know. But we seem to just be drawn to each other. And I love it and also hate it. I hate that the first guy I’ve had feelings for in years voted for Trump. I hate that I can’t even imagine telling most people I know about him – a little due to age, but mostly the politics.  I hate that he’s so predictably bad at communication that he leaves me on edge. But I also really enjoy the feelings of butterflies around him. The relaxation. The comfort. That I can disagree with him on politics or talk to him about my activism and he wants to hear about it. And that he seems to know when he has to back off the teasing about politics and respect that I feel strongly and he needs to STFU.

The universe has a sick sense of humor.

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2x in one week with the same guy…

I can’t remember the last time that has happened. Between my own aversion to expectations and the aversions of those I tend to hook up with to the same, it just hasn’t been on the table.  Last night I saw Cat, the Sunday guy, again.  He said I should come over, he’d make dinner, we’d fuck…I said yes.

Anyway, that’s what we did (well, we fucked before dinner).  And I’m not sure how I feel about things. I was over there roughly 4 hours. Most of the time we talked. It was very date-y.  It was nice. And I also don’t know if it’s what I want. But I enjoyed it. But I’m also “meh” about whether I want it to happen again. The sex was great. So great. Less intense and long than Sunday, but hey, it was a weeknight. But he’s *great* at sex. He’s kinky and dirty and respectful and I love it. He’s also genuinely a good guy. Smart, seems older than his age, respectful…

So I’m going to see what happens. He’s already told me that he’s been accused of being super super intense and then standoff-ish. Whether this works for me or not, who knows. Whether I care or not if it works for me…I don’t know. Though I wouldn’t mind some more sex with him.

Tonight I might be meeting a guy I’ve been talking to for something like 18 mos about hooking up…

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 😉

Trump Hat Guy is back…

Ok, admittedly when I said I was done, I was, in my mind, not necessarily forever done. More just, done with not knowing wtf was going on.  And tired of it. Unlike the other guy I got fed up with the same day, who scared me b/c of his anger, THG just was, well, a 27 yr old guy – poor communicator (oh, and last night I learned he’s, um, 26. I don’t know why I thought 27).

Yesterday afternoon, I got a text from him… “This sucks”. My response was that it did.  But I don’t have the patience to sit around and wonder if he’s going to text back or show up. That I still liked him, but I’m at a stage in my life where I’m just done with those kinds of games and how they fuck with my head.

I was with a friend and she was asking what I wanted when I responded. I said I didn’t really have an end game other than buying into the Dan Savage theory that you should leave them better than you found them when you’re the older/more experienced person. And I’m clearly stating what I can’t deal with and not trying to hurt him.  So he responded that he likes me too.  And asked if I was free…which I wasn’t (was going to a wedding as my friend’s +1).  Anyway, we had a few more texts that he’s not trying to play games (and I truly didn’t think he was…I just thought he was young, hadn’t learned good communication skills and probably was used to being bitched at whenever something wasn’t perfect, rather than accepting that life isn’t always perfect).  So, I agreed that after I went to the wedding, I would text him.

So I did, and this became sort of a situation of me deciding to trust him, be annoyed, but still keep in mind I wanted to see him. I left the wedding around 10 and told him I was on my way home. He said he was out in a neighborhood relatively close to me with his brother and would come over.  Then I learned that getting his brother to leave the bar was kind of an issue (and, to be fair, I can’t judge this too harshly – his brother has some special needs).  And apparently, unbeknownst to me, THG’s brother insisted that he get driven to get dropped off at some chick’s place 1/2 hour away or more.  Apparently this was sort of a fluid situation and wasn’t the original plan. But, of course, he doesn’t do a good job communicating with me. So, he showed up nearly an hour after he said he would (sigh). He did explain. And we talked about that I just needed explanations most of the times, and silence makes me worse.  And he acknowledged he’s terrible with time and with communication (no surprise), but said he would work on it.

And, I let him stay over. Sex wasn’t as crazy as the past times, but it was still excellent (I was tired).  We have great chemistry and I just like touching him. I didn’t freak out like I did when the other guy stayed over. But I did have trouble falling asleep. I think since I had been up past my usual bedtime, it was made worse. And then I started thinking about sleep, which doesn’t help. Eventually I took a sleeping pill. That knocked me out. But I never felt panicky or wanted him gone. I just wanted to sleep. And I wasn’t annoyed by him in the morning (a big deal to me…I get very annoyed when I wake up and someone is there).

So, we’ll see. He told me he predicted in a month, we’ll be hanging out a few times a week. But we both agreed we suck at relationships, so we’re not going to worry about that.  I guess THG is back…we’ll see how long this lasts.

Feelings are dumb

So, as I mentioned Monday, somehow I have, you know, feelings for Trump Hat Guy. Despite every reason not to have them…somehow, yeah. I mean, I recognize intellectually that I barely know him, most of the feelings are based on just a gut response that is attraction/chemistry, but I still have them. We’ve all been there, right? But somehow I thought I was past that part of my life where stuff like this would sneak up on me because it has literally been years since I had those types of feelings for anyone I’ve met. At most I’ve had a passing fondness or 24-hour crush.  This is a “let me google him” crush. Ugh.

So, the stupid feelings…we exchanged a few texts on Monday. And then silence. So, in my head, I’m like “I bet he’s just playing a game…what happened…ugh” and I was kind of sad yesterday about it.  Until I got a text from him last evening that he’d been swamped at work. Still wants to hang out. He’s around all weekend, but hopes to see me before then…and then I’m happy.

Like, seriously. I should not fucking care if a 27-yr old guy who (ewww) voted for Trump in the primary texts me back. This should be about fucking and nothing more. But somehow the universe has a sense of humor and he’s the one who has captured my interest…sigh.  I guess I have to let it play out.

A weekend of exactly what I expected and not so much…

Ok, I’ll get the boring out of the way first.  So, for the past year+, I’ve occasionally exchanged messages with a guy who I just couldn’t cut off the potential list entirely, but he didn’t entice me enough to really try to meet. I couldn’t put my finger on it. He was physically my type. And he seemed nice enough. But I guess he just seemed a little bit more selfish than I typically like in a hookup. But…nothing was concrete in realm. It was just a sense I got.  For whatever reason, I messaged him last week and we decided we could meet up on Saturday.  I had a haircut, he had a friend coming in town, so time was limited. And, I’ll be honest, I ran errands and stuff and didn’t try to maximize the time we had.  While I’m typically not a fan of just going over to a guy’s place, we had messaged enough, and he had been chill enough, that I decided it was fine.  So I did….and he was exactly what I expected physically (a good thing).  We chatted a bit and started hooking up…and it was fine. But nothing great.  He seemed more interested in my giving him a blow job than me having a fun time (I mean, I do give good head, so I can respect the desire, but come on…).  He wasn’t rude about it. I just left like….meh. That was exactly what I expected. It was kind of fun, but not really fun, and I don’t regret putting him off for so long. Oh well.

But I had fun plans lined up for Saturday…which totally morphed.  Originally I had been chatting with two bi-curious/leaning/interested guys separately. What they were saying they were into was so similar that I decided to throw out a 3sum meetup for Sunday. They were both in.  Guy #1 was messaging all weekend how excited he was. Guy #2 starts messaging late morning on Sunday…I put them in a group chat and they seem to be totally hitting it off…Then Guy #1 has to deal with a towed car situation (his car was apparently towed the night before). And he’s not sure he can make it.  So…I offer to Guy #2 that I could message Trump Hat Guy b/c he’s bi-ish.  I didn’t actually expect to hear back from THG b/c I hadn’t heard from him in a couple weeks (we had had plans to meet up, but he was stuck at his parents’ house for Father’s day…and then just nothing).  But to my surprise, he responded almost immediately that he was thinking about me, he’s interested, he thought I was mad at him…Anyway, he’s interested in the situation, but nervous about whether he’d be into Guy #2.  Due to Pride Parade traffic, Guy #2 gets to my place no problem. THG gets stuck and it takes forever.  Guy #2 is nice. But meh. He’s a good bit chubbier than his photo and I have kind of zero desire to fuck him.  I might be able to do it if he brought a hot 3rd to the table…but I knew THG wasn’t going to be interested. So, we have a beer, chat a bit. And finally I find a way of saying that I really don’t see it being a good fit and I wasn’t comfortable. He asked if he should leave and I said yes.  I hate doing that, but it’s got to be done sometimes.  Not a minute after he leaves, THG arrives.  And he kisses me and it’s like fireworks all around.  We do have great chemistry.  So we sit down, talk awhile. We talk very very easily and comfortably.

At some point, we head to my bedroom where, of course, the sex is amazing. I mean, it’s incredible. And then we hung out and talked some more, playing some with my dogs, and then head back to my kitchen to eat something.  So, all told, he was at my place nearly 4 hours and we probably had sex for an hour or less. We talked the rest of the time.  He told me there is nothing about me he doesn’t like.  I like him.  And what the fuck! He’s 27 and voted for Trump in the primary (admits he may not in the General). I mentioned voting for Bill Clinton in my first election and joked he must have been 2 at the time…no…he was fucking 3 yrs old. Not 2. 3!  He assured me age doesn’t matter to him.  He mentions possibly meeting his brother. And like, I’m still interested. One thing I have managed to do for years is be in control of my crushes. If I don’t hear from someone, no big deal b/c there are tons of guys out there. And…I actually want to hear from THG. Not just to have sex (which I do want to have lots and lots of sex with him), but also because he interests me. He’s wicked smart, but he sees the world through a different set of lenses than I do…but it is a considered set of lenses (believe it or not), and I get curious how he gets there.  But then I talked to him about why a lot of older feminists are rather strident and the types of sexual harassment I have faced in my career…and he totally took the information in and was shocked that things that I took as “normal” actually happened.  So he’s not dismissive of such things, just underinformed. And open to info.

So fuck me. I actually like like a guy. And it happens to be a 27 yr old Trump supporter. Of all fucking people. We’ll see. As I told a friend, if he ends up being terrible, I can console myself that he’s a Trump supporter and 27.  And if he’s great, I suppose this is the fun plot twist that a Hulu Television Original based on my like would throw into the mix.