Ahhh. Birthday sex

Yesterday was my birthday and I had plans to hang out with a friend, so didn’t think I’d fit birthday sex into the day, so I didn’t even try (though I a number of men I had been messaging, but hadn’t met, offered).  I hadn’t heard from Ass Man since last week, but I wasn’t really worried. I know he’s busy and I made it clear I was.  But I shot him a message yesterday and he promptly responded and asked what I was doing that night – that he had a work thing and would I be available after.

Since the timing of his work thing roughly lined up with my plans, I figured it was worth a shot at seeing him, and getting some good birthday sex. My place was a disaster, but I figured he could just deal. He wasn’t coming over to see my organizational skills…So as I was walking out of dinner to head home, he texts to say his work thing was wrapping up. Perfect. He said he would come over after.

Of course the trains didn’t really cooperate and I ended up walking home from the station that isn’t as close to my place as the one I prefer. Not a big deal, but it was hot and muggy. And then I had to walk my dogs…also hot and muggy. So by the time he got to my place, I had managed to feed my dogs and pick up the most offensive of the mess, but I was sort of drenched in sweat. I wasn’t that worried – our first date had us caught in the rain and he kept saying how hot I looked. But, eh, not ideal.  He, on the other hand, looked amazing. He was in a casual suit and just looked…so fly and so hot. But he didn’t seem to care.

We started making out on my bed and he put his hand on the back of my head as I was sucking him off and he asked why I was so wet.  I had a moment of “crap…sweat is so gross” feeling, but I just said I was sweaty from the train home and walking the dogs and his response was “I like it. It’s hot”…perfect 🙂 Anyway, if possible the sex was even better than the 2 previous times. At least on my end. I don’t think he had any complaints. He hung out for awhile after, just chatting. I do actually like him and I think we’re on the same page re: enjoying being single and not really feeling comfortable in relationships. I told him about the assumptions people at work make about me for being single (I think a lot of people assume I’m a closeted lesbian), and he said he was sure he’d end up in the same boat since he doesn’t see himself ever marrying or being in a LTR serious enough that work people would know her. It was good…

And a good way to usher in a new year. I keep wondering if at some point I just sound too old, but so far, the young guys have zero issue with my age. I’ll probably do a post about aging (and sex) soon. It’s not what I expected when I was younger.

Two times in a week…we’ll see what happens next…

On Monday, I got a text from last friday’s hottie (who I guess deserves a name now…I guess Ass Guy). He asked if I could get together Tuesday or Wednesday after work.  It surprised me b/c he’d made it clear earlier that he didn’t like weeknight plans, so I guess he *really* liked the sex. Which, of course, made me nervous. But I also wanted to see him, so he came over Wednesday.

I offered him a beer and we sat down on my couch…which lasted all of about 2 minutes before we were making out, I was soon naked, he followed soon after and his fingers and tongue gave me an amazing orgasm.  After that, we headed to my bedroom where I had gotten a bunch of toys out…which we ended up ignoring b/c we were so focused on each other. He actually apologized for that, which was pretty funny. I just got them out b/c he asked for them, I’m perfectly capable of toy-less sex. And I definitely did enjoy it.  He’s so freaking yummy and I love how he smells.

After sex, we hung out talking a bit about books and travel and my dogs jumped up on bed…(and he wasn’t weirded out that they were on the bed). So, of course, I’ve spent the last couple days crushing on him. He did make it clear that he wants to see me again, and I would be down for something regular with him.

But in the meantime, I have a date tonight with a new guy I’ve been messaging for awhile. My birthday is Tuesday, and I’m also interested to see if a new age range changes who contacts me.

 

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. 🙂

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.

The logistics of arranging an MMF…

MMFs are my favorite sexual situation. They just turn me on and I don’t find having an extra person weird or awkward in any way (I kind of do with MFF).  But they’re the hardest to arrange IMO. Finding 2 guys who are on the same page with the amount, type, or limitations on physical contact is…daunting. And then, when you do, getting them BOTH to show up at the appointed time is even more difficult.

Last night I had set up an MMF with Hot Bi Guy and a guy I had messaged with in the past who reappeared who just looks so all american innocent…but, around 6pm, I got a message from the new guy that he had a million things in the air and he wasn’t going to know if he could make it until much later. Well…I had also been in a 3way chat with Hot Bi Guy and another guy who I had been messaging forever. Since all american innocent guy had asked first about setting something up for Tuesday, he had first dibs on my time. But with him looking unlikely, I needed an answer b/c at the same time, the other new guy was messaging me asking if by any chance things had fallen through and he could make an appearance. I didn’t really want to say to all american guy “are you in or are you out bc I have other options”, but finally he gave me an answer asking to reschedule. Whew. It was only 6:15 and I could ask the other new guy (he’ll be Teacher Guy from now on…b/c he’s a teacher) and Hot Bi Guy if that could be the new situation for the night.

Hot Bi Guy just rolled with it. He’s like…my dream 3rd for MMFs. He’s fucking gorgeous. Truly. I am seriously fine if he just comes over and lets me talk to him so that I can look at him. And he’s really nice and laid back. And he’s fine with whatever another guy is into…and he is cool with awkwardness and he’s just a perfect third.

Teacher guy showed up first, ostensibly to have a drink and get to know each other since we hadn’t met and Hot Bi Guy and I had.  I actually thought he meant have a drink, but within 5-10 min, my pants were at my ankles and he was eating me out. We eventually made it to my bedroom where I ended up naked, while he did everything he could to me with his clothes on.  After I’d cum a couple times, Hot Bi Guy arrived. I was naked, Teacher guy was close to it and on top of me, so he just laid down next to me and joined in.  Even though Teacher Guy had said he was into experimenting with a guy, he really didn’t seem to be. Which, while disappointing, was still fun as then all attention was on me.

Afterwards, Hot Bi Guy asked Teacher guy how old he was…Teacher guy is 25 and Hot Bi Guy is 27. I quickly did the math to make sure I’m younger than their ages combined (yes, I am).  They kind of teased me about that – robbing the cradle and all…but men my age tend to be really sexually reserved in comparison. And not as respectful.

The only awkwardness really was at the end when we were all dressed and Hot Bi Guy and I are chatting about tattoos and medical school and Teacher Guy was like “oh, my lyft is here”. I mean, that’s fine. I didn’t expect a ton of lingering, but he was gone in a second. He did message me after saying he had fun.  So, IDK. Hot Bi Guy gave me a hug on the way out and said “see you soon”…so yay, he seems down to keep on being my 3rd!

I had a moment or two of thinking how odd this is. I’m not someone anyone would expect would rush home from work to get ready for 2 guys to come over to see. And yet, it just seems like a way to have fun that is low pressure and high enjoyment. So it doesn’t actually feel weird. It would just sound crazy to anyone who knows me who doesn’t know this side of me (and maybe to a few who do).

Productive Saturday…and the Return of Trump Hat Guy

Yesterday morning I traveled about 2 1/2 hours to speak to a group about activism in the Post-Trump World. Then I went home and fucked a Trump voter…sigh…(and then someone after that).

After Wednesday, I decided to get in touch with Trump Hat Guy about a 3some with the super hot bi guy who was part of Wednesday.  THG was into being fucked by a hot guy with a nice cock and, well, super hot bi guy is about as good as it’s going to get for that.  And since I prefer bi MMFs…and super hot bi guy was into the idea, decided to reach out.

THG was moderately in touch for a couple days, but annoyingly uncommunicative.  Then yesterday on my way back from the group, I got a text from him. He was interested in the 3some…but he wanted to see me and hang out with me before anything with a 3rd.  I had plans last night with someone I was actually interested in meeting, which I told him…he said he would come over before that if I’d let him. I was skeptical, as he *never* has ever shown up on time. and I didn’t have a lot of time, so…I didn’t see how that would work.  But I told him if he was at my place at 5, I would give him an hour or so.

And he actually showed up at 5:01 (I’ll take it). He walked in the door and we just started kissing. It didn’t feel like it had been 6-7 months. It felt like we had just seen each other. And of course we were fucking and then naked (yes, we didn’t even really wait) within minutes. After, we talked for like an hour or so. I emphasized that I don’t want the drama we’ve had…I can’t do it. He said he gets that and he promises it will be better. I’m still, of course, wary. And I told him it would take me time to believe that to be the case. He said he understood…and he was also excited that I might go fuck someone else after him if I liked the guy.

After a long day and being well fucked by THG, I wasn’t that into getting ready to go meet the new guy, who I’ll call ex-Hollywood Guy. But he had interested me. He was only 25, looked super hot, and seemed very cool. But I DID want to meet him, so I sucked it up and got dressed (I didn’t shower again…oops). I got there a couple min before him, texted him where I was and when he showed up, he was hotter than I expected and more charming.  Within minutes he was telling me that I was much hotter than my pics and the first person he had met who was. So we had a drink, flirted, and then went back to my place. He was a fantastic kisser, fantastic with his hands…the sex was a little bit less natural than it sometimes is. I don’t know if that was us, his age showing, or just that I’d just been with someone I had a very comfortable sexual vibe with.  After sex, we talked a bit and then he said he’d let me go to sleep (I was grateful)…and I texted THG to let him know that yes, I had fucked the other guy, and he seemed turned on.

So, while some people might be like “omg, you fucked 2 guys in a day, back to back!”, I kind of don’t see that as a big deal. I’m more weirded out that I still have a connection with THG…so we’ll see what plays out. Hopefully I’ll get that bi mmf with him tho…

My perfect Friday night

Superman came over, fucked me, I orgasmed more times than I could count (or just never stopped?), and then he left to go out with friends and I can chill and go to bed early and get up early.

Sad for some? Maybe. For me, perfect.  I like time to myself. I don’t like being up late Fridays. I like getting up early on a Saturday, working out, and having a full day.  And I like sex. I like sex to not interfere with my time to chill out. And this didn’t.  Doesn’t.

And, by the way, being dildo’d at the same time I’m being eaten out is heaven.  Total heaven.

And I’m still riding the bliss of pretty much an hour or so straight of orgasms…