Surprises…

Last night I was supposed to meet a guy from Bumble for a drink. I’m still a Bumble virgin and I thought he had potential…but he had a work conflict, so I had a free evening that I had planned to use to meet someone. So when a guy I’d been chatting with asked me about grabbing a drink sometime, I asked him if he could last night and he could.

I really didn’t know what to expect from him. He looked in his pics as straight-laced as can be, but he looked relatively attractive (if vanilla), but the messaging hadn’t been too vanilla.  He showed up at the bar by my office and, yep! Totally vanilla (honestly, I’m not sure I’d recognize him a line up). Don’t get me wrong. He was pretty attractive, but just…vanilla.  And our conversation started off pleasant enough, but vanilla. Work. Other interests. Etc. Finally I saw an opening to generally mention sex in a general way and that helped move the conversation along to just general talk about exploring and trying stuff, with him mostly asking me questions.

It was time to leave (I had to take my dogs out). And he surprised me by saying he’d pay for the drinks if I paid for a cab back to my place. I wasn’t offended. I had decided along the way that if he wanted to get together again, I would. But I was surprised. He didn’t seem to have that kind of game. But I underestimated him.

So back to my place we went, took my dogs for a walk, and when we get back, started making out.  And it was good. Obviously we ended up having sex and it was actually far less vanilla than I imagined. Nothing too crazy – but some toys were used and he definitely liked to be rougher than I would have guessed (which I enjoyed).

He kept saying how incredible it was and how hot and kinky it was. It was less vanilla than most first time sex. Nowhere near the kinkiest. But he seemed blown away. It was actually kind of fun to what how it seemed like his mind was completely blown by what had taken place. I’m not normally into teaching younger guys the ways of sex…but he knew enough and it was fun to let him act out some fantasies.

I’m guessing I’ll see him again. I think his mind was too blown to miss out on another opportunity. 🙂

Why does everyone want to take care of a snotty woman?

So I have a cold. I think it was the terrible hookup from last weekend (jackass). but it’s a classic cold. Sore throat. Snotty nose. Exhaustion. Not particularly sexy.

And yet…so far 4 different men (3 of whom I have never met) have offered to come over and make me soup and take care of me. Now, obviously, I assume most of them think they’ll get laid if they do. But who wants to have sex with a gross, sick stranger? I kind of get the one who has met me offering…Indeed, he’s the guy from a couple weeks ago who gave me a massage and seems more interested in being boyfriend-y than fuck-buddy-y.  But the other guys? I don’t get it.  Of course this has me wondering if this is about weakness and dominance…

Updates…

So, I haven’t posted anything for awhile because work essentially swallowed me up for a few weeks.  I was out of town, working 15 hour days, and didn’t have a lot of energy for anything.

I would be very confused by Trump Hat Guy if I hadn’t sort of processed and set aside my confusion…despite texts suggesting he really really wanted to see me before I left, he made no effort to do so.  But I got some while I was gone about how he missed me.  And we texted over the weekend after I saw he had texted at 1am Friday night (while another guy was in my bed, back to that in a minute).  He still seems into me. Says he could imagine an open relationship with me potentially in the future. Wanted to be sure I wasn’t heading towards monogamy with someone else…but still hasn’t suggested a time to meet up. I think he’s probably seeing someone who (possibly) he’s already getting bored by. I went though a little bit of jealousy of this until I reminded myself that I am also seeing other people (just in more of a seeing many people type way).  And there is zero reason for me to be pushing something with him when there are real reasons I shouldn’t be into him and there are other options for me. So I’m back in a place of emotional control that I like – if/when I see him again, I’m sure I’ll enjoy it. If things develop into more, ok, fine. If they don’t, totally fine. I trust that he’s interested, to the extent that matters. I just don’t know if he can give me what I want – which is further complicated by the fact I don’t know what I want when it comes to something more than super duper casual. I know that I have the emotional capacity to care and to communicate well.  But I don’t know what I want beyond the moments of good connection that can be either good conversation or good sex or both.  So…does he still offer something I want? Probably. When he stops offering that, then I’ll cut him loose.

Ok, so other “development”, such as it is…before I had to leave town for work, I started texting an openly bi guy (like, just as into men as women, maybe even more into men).  He’s 28. Didn’t have time to meet before I left town, but we kept messaging while I was gone and it definitely developed from ‘let’s talk about sexual interests and other basics’ to something that was more about chatting, actual conversation, sharing, etc.  The last time I had that level of sharing was with my most serious ex years ago…but sex wasn’t explicitly on the table. So, given the fact this went on for more than 2 weeks and I felt very comfortable being open with him, it is fair to say I was nervous to meet him (which we set up for Friday – I got back in town late Wednesday night).  So, Friday comes around and I was less nervous that day because I’d put on the table I was nervous. And that’s all I needed to do, I guess.  He asked if he could bring his dog to my place, since he usually plays with her at the park near his place (he lives about 45 min away).  I said sure, of course…well, his dog ended up being afraid of one of my dogs (for silly dog reasons, but, whatever…she was). And I think she got jealous when this guy (um…I’ll call him Pokemon guy, bc he’s the first one who told me about Pokemon Go) was paying attention to me.  And she barks. A lot.

Pokemon guy was less hot than his hottest picture (I think he’s gained weight since then), but hotter than his least hot picture. And he had a very gentle/relaxed vibe that I responded well to. Basically, I felt very at ease with him.  So, after the dog park, we went to my place and as I was giving him the tour, he started giving me a shoulder rub, which was amazing. And when we kissed, it was very very good and natural.  So, initial impressions were…not the hottest guy I’ve hooked up with by far, but I’m super comfortable with him and kissing is great. We ended up making out on my couch a bit and went back to my room to have sex. Sex had the potential to be good, but his dog was barking like nuts the whole time and it was difficult to get into it. Plus, his dick is small. Like, not the smallest I’ve seen, but definitely small. But his oral skills were very good. I just didn’t relax enough to cum, which is fine. It was still a good interaction. We then proceeded to order food from grubhub on my phone, naked in my bed, and he was very cuddly and sweet and affectionate – little kisses, that kind of thing. And I totally felt good, not freaked out, by the affection. (So we’re into territory I rarely go anymore).  We went back to my couch to hang out while waiting for the food…he tried to massage me, but his dog was nuts. Get food, eat it…and we try some more massaging and his dog is still insane. So we go back to my room, all the dogs follow, his dog wants to be next to us while we have sex. I’m weirded out by this (his dog is big and was right next to us). So we make her get down from the bed, she continues to bark. So…basically, I can’t decide if sex between us would be any good b/c I was super distracted by his dog. And he was super stressed by her too. He said next time he’ll leave her with his parents to watch…

Since he lives kind of far away, I had told him he could stay over, which I almost never allow. And I kind of freaked out. He fell asleep right away and was snoring gently. Not even bad. But I couldn’t relax and I kept getting more and more agitated and freaked out. It was weird b/c I actually liked his body next to mine, but I also was anxious.  So I woke him up to tell him that. He asked if he should leave and I said no (and meant it) and he asked if I could tell him why I couldn’t relax…and I started crying. Not audibly. And I don’t think he knew. But I was surprised by my reaction. I said I didn’t know and did ask if he could try sleeping on his side so that he wouldn’t (maybe) snore. He was happy to comply and cuddled me and I tried to relax. Luckily then one of my cats came up to me and I could cuddle my cat and between talking about my anxiety and having a cat to cuddle, I relaxed and fell asleep. Not that I slept well. I woke up many times. But it was much better. I genuinely did enjoy his cuddling, but I wasn’t sure if it was what I wanted, even as I enjoyed it. I know, not a lot of sense to it.

Luckily he left early b/c his dog woke up and needed to go out.

I’ve been messaging him since. And I like him. I am not annoyed by his messages (a sure sign I’m done with a person). But I’m cautious. THG asked about Pokemon guy (b/c I told him another guy was over when he messaged and he asked about him and I basically said he was a super nice, sweet guy, and sex was just so so…but he was good to hang out with) and whether I wanted a relationship with him or what. I actually am glad he asked (it was the next morning) b/c he made me articulate where I was at – I like Pokemon guy. I think he wants something more serious and monogamous than I do, but I’ve been clear with him about where I’m at.  I’ll let things play out as they play out and *try* not to overthink what anything means. If I’m honest and open, it will be fine.  And I know I don’t want monogamy, even if I end up with some kind of “partner”, so, knowing that keeps me from FOMO.

Anyway, I have another date tonight with a guy actually older than me. That rarely happens. We’ll see!

 

 

Making friends all over…

I have a quick overnight business trip…had hoped to see sexy geek guy b/c it’s to his city. But 2 weeks ago he got asked to speak at something and we’re going to miss each other 😦 boo.  But last time I was in this city, I opened up a dating app and somehow due to confusion over where we were both located, ended up chatting with a guy who lives here. I figured I probably wouldn’t meet him, except he used to live in my city and visits sometimes, but he seemed cool and, well, hot as fuck.  So we kept chatting and when I found out I couldn’t meet with SGG, I let Hot as fuck (HAF) guy know I’d be in town.  It worked out that he was traveling to another city tonight, but had the afternoon free, as did I after I met with a client.  Original plan was to meet for a drink…but my hotel is a boutique hotel without a bar and I said he could just come to the hotel. I figured…I’m in a hotel. It’s MY hotel…

And he was hot. And nice. And well…he was a great fuck.  He has the right physical traits to work it. And somehow he seemed to find the fact I’m very unassuming and innocent looking to be, well, hot.  That I’m not a person you’d expect has a side that is so open sexually.  So he made me feel sexy. Even though I felt like he was out of my league appearance-wise.  And he had all kinds of little moves…he was good. Damn good. But also very concerned with my pleasure.  

This is something I’ve found…the freakier someone’s interests tend to me (at least for men), the nicer they are and the more conscientious of a sex partner they are.  Maybe they know what it’s like to feel rejected? Or they just understand the breadth of sexual experiences? Or they’re not desperate…fun afternoon. Now I’m exhausted and need to work. But definitely worth it. 

Well…welcome home to me…

So, I haven’t posted in awhile. I was on vacation for a couple weeks and leading up to that was busy.  And last weekend was super jetlagged (and even this week).  I did go out with one guy on Friday last weekend, beyond jetlagged. I thought he had potential, but apparently he wasn’t that into me.  Oh well. It is rare for me to be rejected after a date, but it happens.

So, today, I decided to give the comedian from months and months ago another chance.  He’s the guy who cancelled on me twice.  Had he not actually cancelled, had he just ghosted, no way.  And actually I thought no way in general…but right before I left on my trip, he friended me on Facebook. I was curious about that and thought maybe it was just one of those massive FB friending things…after all, some days on Facebook, the “people you might know” seems like a “here are people you slept with or considered sleeping with over the past 15 years…” (seriously, what’s up with that???).  Anyway, I decided to accept the friend request and see what played out. He has over 1,000 friends, so I figured I might just blend into the background if it was an accidental request.  But pretty soon, he started liking some of the photos I posted of my trip.  But still…that was it.  Just liking photos. Here and there.  Since we were now FB friends, I could see more photos of him and, yeah…something about him I just thought was super attractive. He has a great smile and nice face. Sure. But I think he’s sexy. In that way that once in awhile you find someone crazy sexy but know that, objectively, they aren’t nearly as sexy as you think they are. Anyway, finally, he messaged me. And I gave him shit for cancelling on me twice.  He said he was stupid and sorry and he really wanted to get to know me and maybe more.  So…I said maybe.  That the fact I was talking to him at all was probably a good sign for him. But not a definite.

Anyway, he kept up a constant, but not annoying level of interaction.  He’s the type of guy, esp given his profession, who has the cool guy exterior. But something about him made me feel like he actually does have a good guy heart.  I got that impression in messages (and had previously).  So I had a good impression. So, getting back, I actually was into seeing him.  Last weekend, we decided not to meet b/c I had just gotten some tattoo work done and had my period.  I teased him that he just couldn’t deal with my period and he said he could – just that he wanted the first time we got together to be comfortable and with the tattoo healing and period, it probably wouldn’t be. But that he would come over if I wanted. I agreed with him…but was excited to meet him this week, but also bracing myself for a no show.

Anyway, in between I was talking to a guy who I was interested, but not overly so, in.  He asked about Friday after work and since I had no plans, I agreed…anyway, we met for a dog walk. Things were fine. He was more attractive than I thought he would be, but wasn’t my type.  Still, I invited him in.  And after some awkward and very mechanical oral, he said he wasn’t feeling it and I agreed. I felt kind of dumb agreeing – b/c it always comes across as defensive. But I’d already crossed him off my future FWB list mentally.

This morning, he messages saying he was bummed we didn’t click. I was cute, etc.  But he had a friend who was interested and could he give his friend my info. I said sure (I had seen photos of said friend).  So we start texting.  And then the comedian actually comes over! And he was exactly how I was hoping he would be – he was attractive in the way I wanted him to be. We clicked right away.  No awkwardness, or very little.  And we had great chemistry.  Ahhh. After one date with no chemistry and one date of being rejected, it was nice to have that click of attraction.  He didn’t stay too long b/c he was in the middle of stuff for work. But we agreed we should do it again…soon…and have messaged since he left. So I have a good feeling about that.

So I messaged back the friend of the guy from last night…I guess he needs a nickname. Trade-up guy, I’ll call him. Since he seemed to be a trade-up from his friend…Anyway, we’re chatting back and forth and he mentioned he was at a sex shop, like 2 blocks from y house.  So I told him how close he was and, well, invited him over.  Now, I’ve never had 2 guys in one day.  But I still had some energy after the comedian, and since trade-up guy was a friend of a guy who had been decent to me, just no chemistry…I decided why not.  So he came over and was more polished and preppy than I expected. But attractive.  (Going from a comedian to a hedge-fund guy in one day…) Anyway, we did have great chemistry. Different than the comedian, but just as good. Just different.

And this whole time I’ve been chatting with a really interesting guy from a nearby-ish city who contacted me last week.  He is interested in a cuckolding relationship. Something about him interested me.  He’s like a successful, really intelligent (obviously), good-looking guy. And he wants to be with a woman who is sexually open (wouldn’t be for him), and who controls when and how he gets off.  I’ll admit I didn’t necessarily get it at first, but in talking to him, it actually intrigues me and maybe possibly could be a relationship style that works for me.  Maybe.  Helps that he’s in another city. Anyway…he’s been very interested in hearing about my day.

And now I must get some work done.  But it was a really satisfyingly fun day 🙂

 

 

We never met. I don’t actually care about you…

The thing about having a dating profile indicating that one is open to casual sex is that one gets a lot of messages.  Or at least I do.  So I respond to those that seem to interest me.  And sometimes the people I’m messaging with end up annoying me, pissing me off, or boring me before we meet.

Sometimes I have the energy to tell them “sorry, I’m not interested.”  Sometimes I don’t. But if I haven’t met someone, I don’t feel like I “owe” them a break up. Just like you wouldn’t break up with someone in a bar who you exchanged a couple sentences with. Or even had a conversation with.

But guys just keep coming back.  Even some who “end” things with me because I’m not available enough.  Today, for instance…one guy who told me last week that I didn’t seem interested enough (I really wasn’t that interested) decided that he was going to start messaging again.  And another guy who I told months ago that I wasn’t interested texted to tell me he was thinking about me.

Why? Why are you thinking about me? Because I told a sarcastic joke and you thought of it? We never even met.

The thing is, most men don’t get as many messages as I get. So I guess some men elevate me to being something to them that they aren’t to me.

It really is true that men will chase you if you don’t care.  Or at least some men will. And it’s dumb.

Real sex vs. Porn

I have an uneasy relationship with porn.  I’m a highly visual person and I love seeing sexual images of all types (I don’t buy that women aren’t very visual – I buy that women are taught to be ashamed of liking sexual images).  But I do know that a lot of women who are in porn are not there purely by choice.  It’s a messy industry.  Anyway, this post isn’t really about that.  But I guess I start almost all discussions about porn with my conflict about it…

I’ve meant to write about some of the generational differences I’ve noticed in men since my dating pool that I consider ranges from about 25-50.  The pool I’ve had sex with in recent history has been 26-44.  So, between talking to guys in the 25 year age range pool and having sex with an obviously (much) smaller subset, I have noticed some generational differences that can’t purely be dismissed as coming with more years of having sex.

One of those differences is the impact of porn on what men expect sex to be like.  While, I think basically all men (and most women) in that range watch some kind of porn now, the older guys didn’t grow up with porn being readily accessible at any time, any place.  The unfortunate side effect of porn on demand is that there are a lot of younger guys who think hard, sustained pounding is all it takes to please a woman.  They don’t appreciate that variation in speed, intensity, teasing, etc, is all part of the fun.  That isn’t to say some haven’t figured it out.  But they are the exception. But many men seem to think that bragging about pounding me for hours is exciting…

Now, I have a lot of stamina.  And I can go for hours. But if it’s the same thing over and over, I’m just going to be bored at some point.  I think this is where men who had to figure out how to fuck without internet porn have an advantage.  They do know how to mix it up.

So I wonder if there is any good that comes from constant access to porn…I’m not sure.  I do think there are things younger guys are much better about than older men (that are generational differences, not just physical differences in age)…and I’ll try to put up topical posts on those things.

But if anyone has thoughts on whether a constant stream of porn is actually a good thing, I’d be interested.