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.

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.

Fulfilling a 25 year old’s fantasy…

One of the guys I have hooked up with a few times (he was #2 on this day) is a super hot, super nice guy who seems to be kind of struggling with his desire to be nice guy and his fantasies. Since he’s always respectful and kind, and doesn’t really shift his internal issues to me too much (or at least not in a way that bothers me), I kind of like indulging him. I think he needs some help normalizing kinky fantasies as a thing that nice people have, so if I can help, I sort of feel like I’m following campground rules.

For a couple weeks we were talking about his fantasy of walking in and finding me in the shower and asking him to join, so I told him we could make that happen.  So a couple weeks ago, I told him to let me know when he was on his way and close and I’d leave the door open…

I wasn’t sure exactly how his fantasy played out (and he had never even had shower sex in any way). I felt like I was in the shower forever before he came into the bathroom…naked. I didn’t expect that, but wasn’t disappointed.  He got into the shower and I didn’t think he’d ever want to get out.  To be honest, I was kind of tired of being in the shower, so eventually I got him out.  And then he wanted to have sex on my couch b/c he has a couch thing…which was fine (other than it makes it much more difficult to keep my dogs occupied).  I did find that it was much more fun to do reverse cowgirl-ish riding while on the couch – how did I not know this?

So, it was an interesting time. I mean, I can’t say it was the most fulfilling sex ever, but I kind of felt like I was being a good sex mentor.

Massage + sex? Very relaxing

I’ve been buried at work and haven’t really had any time to try to meet up with anyone for sexual release.  I just can’t deal with scheduling and flakes when I’m already stressed. But on Thursday a guy I had been talking to on and off for about a year messaged me and offered himself up at my convenience over the weekend. He’s married, but totally open relationship (I *guess* he could be lying, but he has a very very rich backstory if he is…so I believe him).  We had a very friendly vibe, so I wasn’t worried he’d be weird and I said he could just come over Sunday morning.  Normally I prefer to meet someone out in public, etc etc, but I didn’t have the time and we had even spoken on the phone. If he was going to be a weirdo, he had had time to show that and he hadn’t.

So he showed up yesterday morning and, as he requested, I wasn’t 100% dressed – I was wearing a long (but not too long) button up shirt. This guy (Massage Guy, from now on) is my age and I realized how rarely I hook up with men my age because, even though he was in good shape and kept himself fit, he looked so much older than most of my partners…in other words, he looked good for his age, but was my age.

We went to my bedroom, chatted a bit, and before long, I was on my stomach and he was licking my ass.  Then he started massaging me, which was highly appreciated, given that I’ve been super stressed.

Eventually we fucked and it was very…friendly. I wasn’t remotely uncomfortable, but it was more like friendly fucking than intense fucking. It’s always interesting to me when that’s the dynamic b/c we make sex so taboo and then here was this guy who was just…nice…and he’s doing all kinds of dirty things to me and it just seems friendly.

After I came a few times, he flipped me over, lubed up my ass all over, and then rubbed his cock between my ass cheeks until he came all over my back…and then continued to massage me with his cum. Which, typing that out sounds so deviant…but it was just really relaxing and nice and I enjoyed it.

We talked about more erotic massage and what else we can do in the future. He’s not the type of guy that I think I’ll be spending tons of time thinking about, but he was easy, nice, friendly, and a good person.  Definitely a good way to get rid of some stress before I enter 2 weeks of work hell…