He actually traveled about 4 hours roundtrip to see me…

About a month ago, I got a message from someone who lives in a city a couple hours from me. It’s not a bad drive, but since I don’t have a car, I sort of responded without expecting much. And he was one of those guys who I couldn’t tell if he was hot…or not. He didn’t have any shirtless pics, but it appeared like he had a good body and a nice face. But he was bald (and I like hair). But for some reason, I responded. I guess I was bored (at least he was in my age sweet spot – 26-31…he is 30).

I was swamped at work, but over a couple weeks, we developed a friendly and flirty messaging thing. I could vent over social justice issues and he got it. But sex was also very much on the table. Originally we had planned to just meet when he was going to be in my city for the weekend of Sept 30 to see a friend, but when my work cleared up, that seemed to be really far off.  So finally I said I woudn’t be weirded out if he wanted to meet earlier.  So about a week and a half ago (I’m behind on my blog), he took the train down to see me.

When I woke up that day, I got really nervous. What if I didn’t find him attractive (I still couldn’t tell for sure from pics). I thought I would like him, but what if I didn’t want to fuck him…oh well, he was taking the risk.

His phone was wonky, so we agreed to meet at a fountain near my office when his train got in, in case his phone wasn’t working.  I got there before he did and was sitting doing something on my phone when he walked up…and I was very pleasantly surprised. He was taller than I thought he was and it was obvious he had a fantastic body. And even tho bald usually isn’t my thing, he was really attractive with incredibly sexy lips.

But it was obvious he was shy. He had told me he was, but I guess because we had chatted so much on Kik, I just assumed he would be less nervous. It wasn’t awful or anything, but I couldn’t tell if he was disappointed by me in person (usually guys tell me I’m more attractive in person than in pics, but who knows what a person likes).  We went to my place and took my dogs for a walk. I was aware that we sort of had a window of time to do…whatever…before he had to take the train back (I had told him that I preferred not to do a sleep over the first time I met someone).

After the walk, we sat down on my couch and I was trying to read the vibe…when he leaned in to gently kiss me. And his sexy lips felt soooo good. He was far less…aggressive sexually than I am used to. Not that he was tentative or lacked confidence.  He just was patient with pacing. After we kissed awhile and things got a bit more intense, we went to my room. I should have written this close to when I saw him. I do remember that I had an incredibly intense orgasm when he was going down on me (kind of unusual for me). And I knew he was super into the blow job I gave him. I knew he liked ass play, so I was fingering him too (but, tbh, I never know if I’m doing that right).

The sex was really good IMO, and I could see a lot of room to explore more with him (but he had to get to his train…I did pay for his lyft to the station since he came in to see me).  He messaged me that he had made the train and we exchanged a couple messages, but I couldn’t tell if he was into me or if I was just fuckable enough.

And for like a week, we only exchanged a few kind of awkward messages. I am well aware that men enjoy the chase quite a bit, so once you’ve fucked them, messaging drops off. And that’s fine, but it does make it difficult to read. So I just decided I wouldn’t initiate anything and if I didn’t hear from him, I’d, of course, live. Last night I saw a message from him pop up – he had his new phone set up and it was back to how messages had been before meeting. Very flirty. And he told me he’d been thinking about the blow job a lot and that he could have stayed at my place all night. So, we ended up talking about other stuff he’s into trying, and I said next time he can stay over if he wants…which he seemed into. So I kinda think he was trying to read what I thought about things while I was trying to read him…And it is flattering that I was worth that kind of round trip.

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Mmmm…Evening with yummy guy

I have renamed “Ass Man” into Yummy Guy because, well, I find him so unbelievably yummy. He somehow is incredibly hot and sexy and still has the sweetness of a puppy. He’s a perfect fuck buddy. He makes me feel incredibly sexy and interesting and I still am fucking someone who I would have thought was out of my league. It’s perfect.

Anyway, I hadn’t seen him for awhile. We had exchanged some texts about meeting up, but he was swamped with work. Then I was buried with work…but my stuff was kicked into December yesterday afternoon and I immediately thought of him. So while I was still on the conference call about arrangements for work, I texted him. He texted back immediately and said he was thinking about me (whether he was or not, I appreciate that type of response).  So he suggested last night and I was game.

He asked (if I was willing), could I put on some lingerie and he had a thing for thigh highs…So I put on some fishnet thigh highs, and some very classy, but very sexy lingerie, and met him at the door in an oversize man’s shirt and that. He appreciated that. Very much. After weeks of eating shit food at the office and not working out and feeling gross, I very much appreciated the way he looked at me. And, well, he looked hot AF.  We went to my kitchen where I was going to pour us drinks, but ended up with his cock in my mouth and then fucking in the kitchen before I could do pour anything. We then went to my bedroom where he asked me to put a butt plug in while he fucked me (which I love…and that definitely made anal later on a lot easier to get into more quickly, though he is the best at anal).

After, we hung out a bit talking. I truly do enjoy just talking to him. At one point, he went to my bathroom and I could hear him talking int here and was confused – he went in naked and I didn’t think his phone would be in the bathroom. Turns out he was talking to my cat who happened to be in there (this is the part where he has the sweetness of a puppy). Too cute.

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).