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.

 

Definitely a fun week

Work has been pretty busy lately and I’ve had a fair amount of stress, so I’ve taken a teeny tiny step back to try to have some fun (I’m writing this between paperwork I have to finish for my real life and work).  I had a surprisingly good date/sex on Wednesday and on Thursday a guy that had grabbed my interest asked about meeting up.  In retrospect (after last night’s date), I’m not sure what it was that I found all that interesting about him. But I had a good gut feel that we would get along.  He was new to online dating and said I was the first person he had even talked to.  We agreed on last night and even tho we were meeting a little later than my morning-self likes to meet (only 8:30, but I’m not a night person!), I didn’t want to reschedule  I wanted to meet.

I told him the part of the city I live in and he suggested my favorite nearby bar, so that seemed to be a good sign.  I got there a couple min before him, found a seat at the bar, and was a little nervous.  He had asked me out before he saw my face (my online pics don’t show my face) and I was a little nervous that after he saw my pics, maybe he didn’t know how to say “I’m not interested” (not that I get that a lot, but it happens, and that’s fine – we’re talking about sex. We need to be attracted to each other).  And in his pics, he looks pretty hot, had a great job, and all around seemed like a guy with options. So when he walked in and after the initial introduction, immediately said “you look good”, I kind of breathed a sigh of relief.  Conversation was easy and, being the awful flirt that I am (or think I am), I was trying to make some contact with my knee against his leg, but I wasn’t getting much physical touch in return, so I was slightly concerned.  But then he suggested we take it to another bar (my favorite was oddly loud), so we decided to go to my 2nd favorite bar down the street. It was already late-ish (for me), like 10:30, but I was really enjoying myself.

I *assumed* he was into me when we were going to the next bar…but it was raining, he didn’t make any attempt to touch me, and I was telling him this story of a bad date where he asked me on a 2nd that interested me in topic, but not in company, and he started to say we should do the date in question…and then stopped himself and just said “you should go do that sometime.” So, mixed signals. But then when we got to the next bar, he became a little more clear. My sundress had a small opening at the low back that he kept touching and when I told him I had never seen Game of Thrones, he invited me to watch it with him any time. So at this point, the question for me was just whether he was going to feel comfortable with sex on a first date or, being new to internet dating, would feel he had to wait. We had a drink and decided to leave, which I was fine with as it was 11:30 or so, but I also was really enjoying talking with him and flirting with him and didn’t want the night to end. (Which, again, weird for me. I like to be asleep by 11:30)

We stepped out of the bar and it was pouring. He asked me what I wanted to do and I said “I don’t mind getting wet”, he agreed, so we started walking towards my place holding hands. And he finally kissed me. I was kind of waiting for it at bar 2, but it was pretty perfect in the rain. He was a very gentle kisser and I started thinking what his lips would feel like elsewhere…along the way, we stopped a few more times to make out and he commented how hot I looked in my dress (at this point, it was totally soaked and clinging everywhere…and I wasn’t wearing a bra).

I still didn’t know if he’d come in when we got to my place, but he made a joke about getting out of his wet clothes and I said “maybe you should”, so…that was that. It was decided.

Of course my dogs and cats decided last night was the night they all wanted cuddles, but he had a good attitude about it and the sex was still hot.  Unlike my usual M/O, I had not discussed with him any particular sexual interests, so I was going into it more blind than usual.  Pretty much right away, he dove into ass play (pretty literally), which I do love, and he was great at it.  So when he asked if I wanted him to fuck my ass, I said yes (which I haven’t done since my 4some).  And…it was amazing.  He was very good at it and I came pretty quickly.  Then we moved along to fucking and oral and more fucking….and finally I had to tell him I was exhausted…so he got dressed into his wet clothes and I decided to stay naked…I was helping him find his socks as he was waiting for the uber, walking ahead of him when he bent me over my bed and started licking me again and then started fucking me and had to cancel his uber.  It was pretty hot. And since I have a long-standing issue of feeling self-conscious about my ass, I liked hearing from him that my ass just looked too delicious and he needed more time with it (he also talked more about how perfect my boobs are, but I’ve never worried that guys don’t like my chest).  So, eventually he actually got an uber and left, we talked about doing this again, I’ve given him my number, we’ve exchanged “last night was fun” texts today…

I still can’t figure out why I thought I’d like him, but it was probably one of the best nights I’ve had in awhile. I am ridiculously tired today, but it was totally worth it.

 

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. 🙂

Pet Peeve: Falling asleep after sex (but the rest of it was good)

Yesterday I started chatting with someone I’ll call Geek Guy about, well, fantasies, sex. He had one of the ubiquitous shirtless/headless pics on OKC and I usually assume those guys are looking for what I’m looking for, so I’m the one who actually messages with them. When he showed me his face pics after a bit of good chatting, I realized I’d seen him on apps before and had gone back and forth on matching with him, and decided not to. But since were talking…he squeaked in as someone I’d consider. It’s not that he’s unattractive, he’s just not by type necessarily. But it turned out that he seemed nice, intelligent, normal, and kinky, so I figured I was up for meeting and we agreed on today during the day.

We met at the bar close to me and when I walked in, he was at the bar (almost no one was there) and it was…awkward. He was sort of watching the tv and didn’t seem interested in talking. Granted, I had spent all of 5 min getting ready, so I did feel like maybe he wasn’t into me, and I hadn’t decided if I was into him…

But then conversation started clicking and got better. And I decided he was a really nice guy, probably a little shy, and certainly attractive enough to fuck. So, we headed back to my place and it was very good sex, with room for improvement. I did have some great orgasms, but he seemed a little nervous, but he was really truly nice and respectful.

But then….he fell asleep. Like, that’s fine at night. But, after sex during the day I want (1) more sex, (2) conversation, and/or (3) the guy to leave. I don’t want to cuddle and nap.

He totally wants to see me again. I don’t know how to bring this up now “no sleeping after sex”, but this could be a problem.

Sex is the best

I mean, really, it is. Or can be.  I had a couple weeks of strep throat recovery, low energy, and low libido.  But this weekend I started feeling more normal. I was supposed to meet one guy on Saturday, but I got caught up in work (and he was only available during the day) and I asked if we could meet Sunday. Unfortunately our schedules only lined up for a 1/2 hour or so on Sunday, so I met him. He was attractive. Nicer than I feared he might be. But we didn’t have much time. He said he wanted to meet again, but we’ll see I think we all know about that kind of statement. Could be real…or not.

And Trump Hat Guy had talked about getting together….but, of course, he was a flake. He texted some, but didn’t seem to have any time. So finally, I just told him we shouldn’t be in touch anymore b/c he’s just not that nice to me. And…it felt good to say that. Yes, we have some kind of crazy connection in person. And I do think he legitimately cares about me as much as he can.  But he’s not capable of being a nice person to me other than when we’re actually together. Which is rare. And that’s stupid for me to waste emotional energy on that. So. I’m done. I haven’t heard back. I know I will at some point. I just hope I stay strong.

In between, I was texting a guy I had hooked up with before.  He finally found a place in the city and only lives about a mile from me. But he was traveling a bunch. Then I was sick…and we had finally decided to meet up Tuesday or Wed this week.  On Tuesday at about 4, I heard from hot bi guy who was proposing a 3some for that night with a guy who I had messaged with a bunch a year or so ago, but we had never gotten together b/c, at the time, the guy was really only into group stuff and I didn’t have a group to provide. Unfortunately, he got stuck at work and the 3some didn’t happen on Tuesday and, in the process, I had moved the previous hookup to last night.

So yesterday I was in a bad mood all day. I’m just sick of all the societal misogyny. And sometimes it gets to me. It had gotten to me. For sure. But I was also incredibly horny all day.  I was exhausted, got home late, but still wanted to get laid…so finally he came over around 9:15. He was hotter and in better shape than I remembered. Which is definitely a good surprise. And the chemistry was still so intense. We ended up just making out by my front door for quite awhile when he first arrived. He walks the line between being rough and sensual that I really enjoy.  And he’s ALL about me getting off. As many times as he can get me off. In short, the sex is fantastic. And after…I felt like the sky had opened and I could breathe again. I have more patience, less tension, I’m in a better mood…sex is the best. Really. It is.

How is it that 3somes now seem normal?

Don’t get me wrong, this isn’t a complaint or a worry. It just is…I’m a 40-something professional woman who most people would describe as highly engaged in activism, maybe a little weird (people have a hard time with single women who are happy), kind of innocent looking…and yet, here I am, as a “go to MILF” for an incredibly hot bi guy…

So, super hot bi guy said he had a lot of interested guys in 3somes with me. Which just seems weird to me. But, ok! I’m not complaining. I’ve been so busy lately that I haven’t taken much time to just have fun sex…and if super hot bi guy wants to set up something where I end up naked? I’m going to trust the situation. He’s finishing up med school and was on night shifts last week, so we had to wait for the weekend…Saturday he starts texting me options for the evening. Which feels kind of weird. I mean, these are humans. But yes, I’m going to go with the one I find most attractive. And he had a nice cock too…

So, super hot bi guy and this new guy show up at my place Saturday evening. They had smoked some weed before coming over, which was fine with me. I don’t care. We proceeded to have a couple drinks. The new guy seemed shy and maybe a little too stoned, but he was pretty hot (not necessarily my type – a little to pretty boy for me – but I couldn’t complain about the good doctor’s work in finding him).

After awhile, we went to my room. The undressing is always the most awkward part of group stuff IMO.  With one on one, you can easily undress the other. With group, you kind of have to take care of yourself. Or that’s how it has always been….Since both guys are in amazing shape, I had the moment of worrying that my imperfect body, somewhat bloated from my leftover Chinese food dinner, was not up to their standards…but with both sucking on each of my nipples, I quickly forgot about it.

Other than my first MMF  where we literally had all independently made decisions to sleep with each other before we got together, this was the best dynamic I’ve had for a 3some. And definitely the hottest guys, which, you know, is part of the fantasy.  I finally managed to experience DVP, which was really fun, though way more awkward than it looks in porn (again, how am I just “oh, yeah, DVP…fun! But awkward? I am not someone anyone in my office would expect this of. But that’s part of the fun).  Oh, and DVP is also fun, besides being awkward.

By the end, I was done, the guys were done, my bed was beyond soaked (so gross to sleep in that night, but well worth it) and I woke up to a nice message from super hot bi guy about how fun it was…and a message this morning asking if I’m around tonight if he can set something up…

Unfortunately, he leaves for the summer soon. I don’t know how med school works. All I know is that he won’t be around after his next set of boards for at least 3 months, maybe forever (depending on job prospects). But I can definitely say that he will be remembered as the guy who helped create a situation that lil ol’ me never thought I’d be in – not just hot, crazy sex. But hot, crazy sex with 2 guys who I never would have dreamed were guys who would be naked with me.*

*Note, I’m very pragmatic about who is in my league looks-wise and who isn’t.  Pretty people are people I enjoy b/c, well, I am motivated by what looks amazing. I don’t think it it means anything more for me than “why yes, I do like touching you naked”-type excitement. I’m no more or less valuable as a person post-3some with hot guys than I was before. It was just a true fantasy experience.