So, plot twist on the last post: the Pedant told me he could be “coaxed” into riding my strap-on, and I asked him how one might best coax that sort of thing (more to elicit more sex talk than anything; I basically know how to get him motivated to do things already). He ignored this message and instead asked me if I was free tonight. I was in fact just heading home from hanging out with Minx, and had no plans for the evening. The Pedant said that he’d just gotten off work and he wouldn’t be able to spend the night, but he could come by for a few hours if I wanted – and that we could discuss my fantasies more once we got behind closed doors.
Well hot damn.
Turns out The Pedant was just a couple of bus stops away from where I was at that moment, so he told me to get off there and we’d proceed together. I didn’t end up needing to disembark; it worked out that he was right by the bus door and so was I and I was just like “You! Boy! Come here now.”
And our hello embrace…just never ended. He stepped into my arms and stayed there, caressing my back and occasionally pulling me closer, for the entire time that it took us to get to our transfer point. And I laid my head on his shoulder and just kind of desperately drank in the feel of his body for those fifteen minutes.
When we transferred to a different bus – one with more seats available – we sat next to each other and he immediately put his hand on my thigh. Which again I drank up. It’s been unusually long since I’ve seen him and we had that fight or whatever in the meantime so I was feeling pretty pent up. I guess he was, too.
Once we got home, I had to forego my fantasy of immediately slamming him up against the door for makeouts in favour of taking a shower. I’d slept over at Minx’s the night before and was unshowered and smelly. Oh, also I gave The Pedant his belated birthday gift before I forgot. I’m pretty pleased with it: The Pedant is a person who likes interesting, efficient gadgets that he can brag about, so I got him a thing that holds your keys in an organized way, and also a carabiner so he could hang the key-unit from a belt-loop or whatever. Also I got him the extra-long version because he works as a security guard and I thought he might sometimes have to carry nonstandard keys to basement storage areas and shit like that. He seemed quite impressed by my gift, and said it would be really useful and thanked me nicely.
(I didn’t bother to point out that he’d recently told me he thinks thank-yous are dumb and meaningless. Maybe he only meant that he doesn’t like to receive thank-yous but giving them is fine? Or maybe he actually likes being thanked for some stuff and is only denying this out of one of his periodic urges to seem all aloof and uncaring and shit. He scares me, a little bit; once upon a time I thought he was a boy I could take at face-value and it’s since become clear that he’s not; that he has an idea of himself that is wildly at odds with who he actually is, and when I ask him things about what he likes or needs he will mostly say things that support this false self-image and the things may or may not be true. Like how he’s always laughed smugly about how he comes off as an asshole and he doesn’t care, but when I showed him that I’d set his avatar on my phone as a pic of an ass-bruise I once had – signifying that he’s a pain in my ass – he got all quiet and hurt-looking.
(In a weird way I trust him both more and less than I used to. I trust him to do his best at maintaining our relationship, and not to purposely hurt me or bail unexpectedly. But I don’t trust his words that much anymore. I don’t feel like I can ask him what he needs in the relationship and get a real answer.)
When I came out of the shower, The Pedant was naked and just finishing lint-brushing cat fur off the sheets. He started whimpering softly the moment I came up and kissed his neck. A while into making out with him he was all “You can restrain me if you want. I know how much you love to see me in thigh cuffs.” All for my benefit, you see. Totes not what he wanted. 😛
But I had no contradicting plan in mind so I went ahead and chained his wrists to his thighs, feeling mildly manipulated as I did so but not feeling up to pointlessly resisting his idea.
And so we continued playing like that for a while, both of us sitting on our knees on the bed, his hands restrained to his thighs (also at some point I got his collar and put it on him). I suddenly realized that all his moaning had made me wet, and I delved down with my fingertip, got it slippery, and then slid it across one of The Pedant’s nipples, which made him gasp so much more deeply than my previous ministrations. I love when I find things to do that turn him on psychologically as well as physically. Super fun.
Last time he was over, I told him I wanted to make an official rule that he warns me when he’s going to come so that I can choose whether I want the sex to end or not. And so, after a while of me running my lubed-up hands all over his cock, he said “You’d better stop playing with my cock or else I’ll come.” So I diverted my focus to other areas for a while. His asshole was seeming quite erogenous; we’re out of gloves so I couldn’t get too invasive with it but every time I ran my fingers over that specific area it got a strong reaction.
And then he said “I’ll take your strap-on if you want.”
I did want this, but I also really really wanted him inside me. So I made him lie on his back and restrained his wrists to the bed so I could fuck him for a little while. Only then did I dismount and go put my harness on.
I showed The Pedant the dildo I’d bought with him in mind (the Tantus Silk Medium, which is fairly small with no “head” or other bumpy bits – it’s totally just a tube with a rounded end) and asked him if it was acceptable to him. He said that it was. I secured it to the harness, freed The Pedant’s wrists, lay back, and poured lube onto the tip of the dildo so it flowed down around it in a thick coat.
The Pedant straddled my waist…and just stayed there, with the lubed-and-ready dildo sticking up into empty air behind his back. I pulled him down by the collar to kiss me and I played with his cock and nipples and seriously five or ten minutes passed without him making any move to put the dildo inside him. It made me think of stories I’ve heard of people trying to fuck who didn’t actually know what sex was. Like somehow, all this time, The Pedant thought that pegging meant sitting near a dildo, not on it, and maybe while we made out he was thinking “I’m totally getting pegged right now! It’s actually not that bad. And I’m fulfilling Cowgirl’s fantasy! Woooo!”
But of course that’s ridiculous and he does know what a strap-on is for.
We kept on making out and stuff and I was trying to figure out how to gently encourage him to hurry the hell up and get fucked already. I felt that if I asked him whether he was having second thoughts, he would automatically say “no” just to look like a tough guy or whatever; I didn’t want to make him self-conscious. Finally I couched it as dirty talk: “I want to be inside you while I play with your cock.”
This finally spurred him to lift up, rummage behind him for a second, and then slowly slide himself down on my cock. His face and his sounds changed as it slid home so that even though I couldn’t feel my dick, I knew it was inside him. So very hot.
His thrusts were considerably more lengthy than I expected they’d be, actually; when I fingerbang him, he doesn’t like me moving in and out a whole lot but rather prefers me to kind of wiggle my fingers around. But with the pegging there were intervals where he rose and fell enough that almost the entire length of the toy was sliding in and out of him. And his chest hitched and his eyes rolled back and basically I couldn’t believe that I was actually watching The Pedant fuck himself on me. At one point he asked “You love dominating me like this, don’t you?” and I made an involuntary squeaking noise and just barely managed to murmur, “I feel like my heart might actually explode right now” and had to fight off tears. It was just…intense.
I started stroking his cock. At this point he mostly just held still; perhaps thrusting and being jerked off at the same time was too much multitasking for him. I compensated by grinding my hips in a circle in rhythm with my hands stroking him, and that seemed to go over well.
The hand job stopped and started; he got to the brink of orgasm a few times but couldn’t quite get over (or at least this is what I surmised from the way he moaned and tensed up and his cock got even bigger and more rigid in my hands…). The toy slipped out and we re-lubed and kept going. And then finally it slipped out of the harness while remaining inside The Pedant (the bases on these things are really not flared enough for the standard strap-on O-ring; seems like a big oversight).
It would have been difficult or impossible to stuff the base back through the O-ring and I didn’t want to remove the toy entirely from The Pedant’s ass to thread it through the ring head-first, so I said “I guess let’s just do this, then” and kept jerking him off while reaching around to gently wiggle the toy inside him.
“I would really like to be inside you,” The Pedant said, and that sounded good, too. I wriggled out of the harness and he settled himself on top of me and inside me (after a few false starts; his erection was suddenly being a bit unreliable). “Can you reach around far enough to keep the toy secure?” he asked breathlessly. I could, albeit awkwardly. And so he thrust inside me and I moved the toy in and out of him a bit and in short order he came, moaning in my ear and then full-body-shuddering for what felt like ages.
Once he’d recovered a bit, he said “I hope this makes up for me being busy on your birthday weekend” which is such an odd thing to say. My birthday was last month and he’d already come over on a different weekend to make up for it. Honestly I think he really, really needs to believe that he allowed the pegging as a service to me and not because he has any interest in it of his own, and he reached for the only excuse he could think of. He then told me that he comes much harder when we do our usual thing of him on his back and restrained during a hand job. Noted, although he certainly seemed to enjoy aspects of the pegging a lot and I think with practice we could bring that up to the same level of fun.
Then he really wanted the toy out of him, so I carefully pulled it out and set it aside and we snuggled for a while.
And then I had the conversation with him that I’d been dying to have ever since that weird text-fight we had.
“So hey…do you worry that I’m gonna suddenly break up with you again? Like is that a thing that’s on your mind sometimes? Because you said something once that kind of indicates this.”
“It’s occurred to me that you might get frustrated with me again for the same reasons as before and then leave.”
“Things seem to have changed since the first time around, though. Your behaviour is different – you contact me more often now, for one thing – and I’ve kind of developed a new attitude. I dunno; something sorta clicked over and the things that seemed like a big deal before kinda aren’t anymore.”
We talked for a bit about how I prefer steady-ish contact and he didn’t used to give it (“And this bothered you even though you knew I was really busy?” “Dude when we were first dating you were unemployed.” “…Oh. Right.”) and how I perceived his silences as a cue that he must think of me as a fuckbuddy rather than someone he was in a relationship with; I said that even just knowing that he thinks of this as an actual relationship made a huge difference to me and put a lot of my worries at ease. He said that he didn’t understand what these “signals” are of someone only considering themselves a fuckbuddy and I was like “Nope, I call bullshit on that. I was trying to explain to you about the Five Love Languages one time and you weren’t getting it and I asked ‘well how do you know when someone loves you?’ and you said you could tell with [ex] because she would call and text you all the time. So, okay, Logic Boy: if calling and texting all the time means someone’s into you, what does it mean when they DON’T call or text?‘” …I think he may finally have understood my position, then. He’s a bright boy but when it comes to emotional stuff he has the most difficult time putting two and two together…it baffles me.
And I tried to explain to him how just a subtle shift in his behaviour managed to make things align so that I’m feeling good in the relationship now. The pilot light is burning all the time and keeping me warm even when he’s not around. I’m not sure if he really understood what I was saying there, but I capped it off with “My point is, you make me happy. And as long as that continues, I don’t see myself going anywhere.”
“Good to know,” he said.
The Pedant started saying that he should get going (and mused to himself that he should pick up a sandwich or something on the way home, and then corrected himself that he shouldn’t because he was trying to save up money to buy his mother an expensive trip for her birthday), and I was like “Ah, but first…pass me the pink dildo and my Hitachi” and I came twice before needing him to back off.
“Done for the night?” The Pedant asked.
“Well, done for the next half hour, anyway. You’ve given me…a lot of things to reminisce about, today.” I curled up in his arms and added, “I can’t actually remember the last time I’ve fapped to anyone else.”
When The Pedant started saying again that he should go, I offered to feed him first (since I knew he was hungry and yet not wanting to spend money on food). He said yes to this.
In the meantime, his mom called him so he had to attend to that. It’s weird, hearing his conversations with her. Obviously I can’t really know what their relationship is like – I can’t even hear the other side of these conversations – but the few times I’ve heard him speak with his mother, he snappishly answered a bunch of questions from her about which laundry of his needs doing or what kind of tea she should make for him to take to work the next day. It kind of amuses me to picture that she’s just this sweet older lady trying to do nurturing motherly things for him and he’s just shitting all over her. It only amuses me to picture this because I’m fairly sure it’s not the case, or not entirely the case. For one thing, she always seems to ask such a barrage of questions about such simple fucking things. I can see how that would be irritating.
Anyway, The Pedant showered and we ate some food and when he left he said “We’ll talk soon, okay?” and it seemed like it wasn’t just a pleasantry. A few days ago I’d invited The Pedant over for this weekend and he said he was working til Saturday but didn’t yet know his schedule beyond that. I’m hoping he turns out to be free on Sunday and still wants to see me. I’ve been backed up for his attentions and this visit tonight helped with that a lot, but I’m still not reset back to normal yet. 😛