Finally pegged Trump Hat Guy!

Or, well, anyone…I lost my pegging virginity.  So, when THG and I first were talking, pegging came up. So it’s been on the table, but just circumstances didn’t work out. It seemed like a lot of potential awkwardness to take on the first time we had sex, and other times I’ve just gotten caught up in other stuff or been too tired.  But I still wanted to do it and he wanted it. So yesterday I texted asking what he was up to this weekend and we ended up talking about getting together last night. I asked him if he wanted me to fuck him with my strap on and I could tell immediate interest on his end.

In the few hours before he came over, I could tell I was nervous, and I wasn’t sure why.  THG and I have an easy vibe and I wasn’t really worried that things would go badly, but I could tell that I was on edge. But when he showed up, it went away. He had some kind of eye issue going on (I actually truly hope he’s ok…he’s getting it checked out now) and didn’t have eye drops (I did) and had actually never put eye drops (or contact lenses) in his own eyes and was nervous. So I told him that I’d put them in him…which he did comment was a little motherly and weird, but he was desperate. And with all my pets and foster cats, I figured if I just pretended he was a pet, I could do it. So our evening of pegging started with him lying on my couch while I pinned him down to put eye drops in his eyes…(it apparently helped a little, but didn’t solve the problem, unfortunately).

But that did lead to making out on my couch and we went upstairs where I proceeded to take control – which I normally don’t do, but I don’t mind with him.  I got him naked and went down on him a bit. I didn’t know if he was going to let me stop to go put the strap on on, but I shouldn’t have worried.  When I got it on, he immediately started sucking the (very lifelike) dildo, which I found incredibly hot.  Finally I made him get on all fours…we had to do some adjusting b/c he’s fairly tall, but eventually we got a position where I could start getting him ready…I was surprised how little warm up he took (tonguing and fingering) to be ready for the dildo.  Indeed, I was surprised that I actually could have gone quite a bit larger (and I’m going to have to, next time). The thing about pegging from my perspective…it’s all about the idea and the visual.  I mean, I can’t feel it since, quite obviously, the dildo isn’t my own body. But I did find it really hot to be in charge of his pleasure. Eventually he wanted me to stop so he could take care of me, but I wouldn’t let him, which was also kind of fun.  To just be in charge of when I would stop.  Finally I decided it was time and replaced the dildo with a rather large butt plug (that he easily took).  His intent was to fuck my ass, but we just couldn’t get the logistics down. I don’t know why, but it wasn’t working and I really wanted him at this point. He was nervous about regular sex b/c he’s one of those guys grossed out by periods. But since I use the Instead Soft Cup (yes, a shout out to them), I assured him he didn’t have to worry about blood and it was all blocked. Either he believed me or didn’t care at that point and he started fucking me and oh my god…it was sooo good. I don’t know if it was because it had been awhile since I had had period sex or if it was just being turned on by this point from the pegging, but it was amazing…

I’ve mentioned before the different types of orgasms I have, and somehow with our position, I went from a g-spot only orgasm to a full on dual intense orgasm that I totally didn’t see coming and we somehow managed the most simultaneous of orgasms I think I’ve ever experienced. We were 100% in synch and it actually kind of weirded me out a little how much we peaked simultaneously.

After we both kind of caught our breath, he went in the bathroom to check on his eye and said “you’re right – there really is no blood!” So hopefully we don’t have to have this discussion next time I have my period because I really do have annoying long periods that come more than I’d like.

We hung out the rest of the night – ordered some food and while we were waiting, talked awhile and then he fell asleep on my chest as we were cuddling, which I found kind of sweet. After we ate and decided to go to bed, said when we got in bed that he did feel like I actually care about him, and that means a lot because he doesn’t have a lot of people he knew in our city who care about him (he’s relatively new to the city, although he grew up in the general area) and that he liked just eating together and hanging out. I think I have known that he consciously thinks about his image to the wider world, but doesn’t really believe many people know him, but this was a reminder of that. I genuinely think he’s a good person (despite his presidential preferences) and I truly feel respected and appreciated by him. It’s just easy to be around him. And this time, I actually fell asleep in a normal amount of time for me and slept very restfully. When we woke up and his eye was still bothering him, we talked for awhile about where he should go and what he should do and I helped him find an option (waiting to hear from him tho). And I didn’t mind that he was taking up my morning and my day wouldn’t go as I prefer it to go. I guess I like him. Of course, it helps that he finds it hot to hear about me with other guys, so even though I like him, I don’t have to change much (if anything) about my life to have him in it. And whatever happens with him, it’s a good reminder of what it feels like to have that comfort with someone who isn’t just a platonic friend. Who I feel like I can be myself around and it’s not something he puts up with, but it’s what he likes about me.

But….I will admit when I was fucking him in the ass, I did remember that he likes Trump and took a little bit of joy in fucking a Trump supporter in the ass 😉


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