Finally got around to having The Pedant over last night. I knew I wanted to progress further than makeouts with him (finally), but I wasn’t sure how far, and anyway if I’d deliberately decided to fuck him I would’ve been filled with performance anxiety and jittery as hell all night. Better, I figured, to keep my thoughts on the subject vague and just let things unfold naturally.
But then when The Pedant and I were solidifying our plans via text, he said (with a winky face) that he’d bring lube and massage oil. Which freaked me out: was he trying to suss out my designs on him by making a joke? Or just flat-out assuming that I was inviting him over for sex? Or – worst of all – telling me that we were going to have sex without particularly caring what I thought about it?
So this of course led to one of my trademark horribly earnest text conversations that lands in the middle of flirty talk like a bowling ball dropped from a third-storey window, scattering all traces of fun to the wind. But it had to be done. Or, well, I tried to keep it light – I was like “Easy, now. Don’t psych me out” but I don’t think he understood what I meant so it came down to me explaining exactly what I said above: performance anxiety, can’t afford to overthink, not sure what I want to happen, blah blah blah don’t pressure me. And – as I’ve realized I often do to people when they’re not actually there – I began to read too much into his remarks and blew things way up in my head to the point where he started looking like some rapist monster. It’s like when someone’s not around, I forget about the subtle complexities of their personality and just slot them into the closest movie-of-the-week stereotype.
But then The Pedant reminded me that he’s never had a problem letting me be the initiator of any physical stuff, and is more than happy to just follow my lead. And I remembered that yeah, he is that way. He’s always made me feel quite safe with him. Sometimes he says douchey stuff, but I’m like 95% sure he has an autism spectrum disorder and the stupid comments are a failed attempt to be suave like the cool kids. Actions speak louder than words, and his actions have been impeccable. I also remembered that he gives a really great massage and is a great kisser and he’s mentioned in passing that he’s uncut (which I love, and haven’t experienced in years). And somehow, remembering all of these good things, I ended up deciding that I would very probably have sex with The Pedant when he was over. I’m fifty different kinds of neurotic about nakedtimes lately (largely because of Minx, I think) but I figured the neuroses would never go away unless I had decent sex just to prove that it was possible. And in many ways it would be less pressure to get over that hurdle with someone nice and trustworthy but with whom I’m not in love, so yeah.
So The Pedant came over and brought some Swiss Chalet, and once we’d finished eating I straddled him on the couch and we started kissing. Which led fairly quickly to the doffing of shirts (OMG HE IS SO HAIRY I COULD BARELY LOOK AT HIM) and then more kissing and then The Pedant took both my hands and (I thought this was kind of hilarious) plunked them decisively down on his boobs (pecs, chest, whatever) and that’s how I learned that he likes his nipples played with. And he makes high, soft little whimpering sounds when I do it. I was not expecting that. The Pedant has a baritone speaking voice and a commanding presence, so watching him come all undone was fucking crazy hot. I felt…powerful. I felt like I was leading a tiger around on a leash. Also, from my vantage point of straddling him I could totally feel his erection poking slightly into the crotch of my sweatpants and every time he caressed me and made me moan, it twitched. OMG HOT.
At one point he broke off kissing me and just scooped me up into a long, hard hug for a few minutes, and I suddenly flashed back to a bunch of years ago when I was in a phase of hooking up with random dudes. Almost all of them gave me the Long Hard Hug at roughly the same point in the proceedings – I guess they’d been starved for affection and were grateful for the skin-on-skin contact. It’s sweet and vulnerable and a little sad.
And then he was running his fingers over my back and ribs in that way that I love, and the band of my bra was getting in the way so I took it off – and The Pedant became transfixed by my glorious rack and buried his face in it for a while (including putting his mouth on each of my nipples, which I usually hate but he was so gentle that it actually felt kind of nice). After a while he murmured “should I get out the massage oil?” and I enthusiastically assented. He got up, took his pants off(?) retrieved the bottle of oil and all kinds of massages and caresses ensued (for which I took my pants off, too, and I don’t usually wear underwear but I did last night specifically so I’d have that one last buffer zone before actually being naked). At first I sat between his legs on the couch and then I ended up lying on my belly while he stroked and massaged me from my feet to the bottoms of my boxer briefs, and it was lovely.
I think that’s when The Pedant asked “Do you happen to have a hair tie around somewhere? I think I’m gonna need it soon.” And I thought OMG he’s planning on going down on me – which both terrified and intrigued me – oral doesn’t usually work for me (done wrong, it hurts) but when it does it’s incredible.
My head may be shaved, but Minx had long hair and he left some odds and ends behind when he moved out…I scrabbled around and soon found a hair elastic on the nightstand. I turned to bring it to The Pedant in the living room but he had followed me and was now in the bedroom doorway. He pulled his hair back into a high little samurai ponytail and then there was more kissing and I tentatively slid my hand down to grope him through his boxers. His erection skewed to the left and was not huge at all (maybe even smallish, but I really have no perspective in this matter since Minx was hung like a horse). When I slid my hand further down and back to play with The Pedant’s taint, I got some lovely vocalizations in response. Both the moans and the fact that he let me touch him there caught me by surprise. The Pedant had told me once that he’s been anally penetrated and it did nothing for him; I assumed this meant that nothing anywhere near his ass was erogenous for him, either. I also kind of thought that since he knows I’m into assplay, he’d get all flinchy if I headed back in that direction, assuming that I’d try to gain entrance. But nope, he enjoyed what I was doing and wasn’t weird or shy about it. Nice!
As an aside: The Pedant’s body is not like I’d pictured. Clothed, he gives the impression of being slim, but naked he’s more solid and big-boned than I would’ve guessed, and has more of a gut. He’d warned me before that he was hairy but I frankly did not expect this level of magnitude – his chest and back were densely covered in black fur (oddly, he had a clear/smooth stripe down each side of his torso. I was perversely reminded of a burned grilled cheese sandwich with the crusts cut off: white edges and dark everywhere else). So aside from his pretty, pretty face, he’s not my usual type at all. But I did enjoy his muscular arms and legs and OMG HIS ASS was as round and solid as a basketball. Just…dense and meaty and biteable. RAWR.
More making out while lying on the bed. Then I pulled The Pedant’s shorts off and straddled him. Yup, his penis points left to quite an extreme degree. Also, completely unkempt pubes, which I think is a shame. It’d look ridiculous if he shaved them (and didn’t shave his belly and chest too) but I think trimming it to the same length as his belly hair would have been nice. As it was, there were…Muppet-like tufts.
I gently played with his genitals and he did the same to me, through my boxer briefs that I was still wearing. Before he got too far with that, I warned him that my clitoris is insanely sensitive and can’t be touched directly; one needs to move the hood over it instead. The Pedant, in his typical pedantic way, volunteered that he bet with enough lube it would be okay to touch the clit directly and I emphatically replied that no, nothing would make it not painful. “So do you get off from oral?” “On rare occasions…it requires pinpoint tongue accuracy.” That was probably the point where The Pedant opted to skip the cunnilingus and just use his fingers instead. I removed my shorts and let him finger me a bit while I was still straddling him, but that angle always feels kind of weird to me so pretty soon I lay down beside him.
The Pedant’s hand motions weren’t optimal, but I find that as long as a dude is stimulating me pretty close to the way I’d want him to, and not actively hurting me, the excitement of being in a sexual situation with someone will generally compensate for minor shortcomings in technique. The Pedant was spooned up against my side with his bottom arm around my shoulders and I felt like I was solidly cradled by his entire body and he kissed me as he rubbed me in almost-the-perfect-spot at almost-the-perfect-speed and maybe a tiny bit too much pressure and I came. And he still didn’t stop his ministrations so I rallied myself and came again.
Then I jerked him off for a little while (“Is there anything you need me to do? Any particular spots I should focus on?” “You seem to be finding them all just fine already”) and then there was a bit of a lull during which I shyly told him that we could have sex if he wanted. He said that was very generous of me (that wording sounds snarky but his tone was sincere) but at that moment what he really wanted was for me to tie him down to the bed and keep on going with the hand stuff. I…did not know that he liked to be restrained. Hot damn. I buckled on the wrist restraints with shaky hands and as I did so he softly said “You can do anything you want to me tonight” which, again, not a sentiment I expected to hear from him. And completely hot. I decided not to push my luck too much and just resumed jerking him off. I had thoughts of edging him for a while and then climbing aboard and fucking him to the finish, but I misjudged his responses and ended up making him come. His lovely little whimpers never increased in frequency or intensity so didn’t realize he was getting close until pow. It looked like a good one, though. He bucked his hips and kind of gripped one of my legs between his (I’d only restrained his arms) and vocalized loudly for quite a long time.
After a minute or two of me lying there petting his chest, he said “I would like to hold you for a while, if that’s okay” (oh man the vulnerability in that statement just breaks my heart – in the best possible way) so I released him from the restraints and he completely bear-hugged me and wound his legs all up in mine…and fell asleep almost immediately. I wasn’t sleepy so I just lay there with my face pushed into his chest, thinking random thoughts and feeling him breathe. Occasionally (especially if I shifted my position at all) his legs and arms would tighten around me like he was trying to prevent me from getting away.
Frankly, I wish I had been sleepy because The Pedant seems to have a magical cuddling alchemy with me – I felt perfectly snug and comfortable and it would have been wonderful to drift off to sleep all wrapped up in his body. But nope, I just lay there awake and marvelling at how well the two of us fit together and feeling amazed that The Pedant is even a snuggler at all (he doesn’t seem like he’d be one).
After maybe twenty minutes or half an hour, he awoke, realized that the parts of me he wasn’t wrapped around were feeling a bit chilly to the touch, and pulled the blankets over us. And soon after that he started giving me another hand job. Unbidden! And after having had an orgasm himself (which for most guys is the death knell on all sexytimes until they’re horny again)! Goddamn.
Apparently I’m not in good enough shape to have that many orgasms, though. I mean, in order to bring on an orgasm I have to flex my legs and stomach really hard (more so if I’m compensating for a newbie’s lack of skills), and I was so worn out from the first two that I couldn’t maintain the flex for long enough. I mentioned this difficulty to The Pedant and we got into a brief conversation about health and working out that led to him telling me that rock climbers’ muscles are the best – and he knows this because he dated two different chicks who rock climbed and they were super firm and hot and etc. He was still stimulating me while he talked, mind you. I gave him a condescending pat on the head and pointedly said “If you’re gonna tell me a story right now, tell me one about you blowing another dude.” He got my point and shut up…but I still couldn’t climax. Finally, I asked to take over and my own familiar stimulation got me there while The Pedant kissed and caressed me. It’s worth noting, though, that The Pedant was catching on to what I like very well – his technique that third time was much improved. I’d just burned out my leg and stomach muscles too much to get over the edge, is all.
By now it was 10pm. The Pedant craned his head to see past me to the clock on the nightstand and said he’d like to stay the night but really should go home because he had to work the next day. (And for like the fifth time that night, I was astounded by the behaviour of this boy. He really does come off as an aloof, cynical asshat in day-to-day interactions, and yet he’s a whimperer and a snuggler and apparently likes the idea of sleeping next to me…wow.) I felt perfectly fine about him leaving at that point – I had no urge to cajole or stall or ask for “just a bit more cuddling” or anything – but he didn’t actually get up or get dressed; he kept lying there as though he hadn’t even said anything. (He didn’t end up going until 1am!)
So we kept lying there and touching and talking, and the topic of Frisk Week* came up and he asked me when my next one was so he could come over and take advantage of my increased interest in penetration and I was like “Actually, it’s pretty much now” and he was like “I wish you’d told me that before I was spent!” And I shrugged and said that I was enjoying playing with him manually so much that I hadn’t wanted to stop and switch activities (in retrospect I realize it’s a relief that I initially offered sex and he asked for a hand job instead…I probably won’t be too compatible with a boy who thinks penetration is the be-all and end-all of bedroom activities).
Slowly, talking segued into kissing which segued into me lightly stroking his penis – more because I enjoy the texture than anything – and The Pedant slowly got hard. “Do you still want to have sex?” he asked me. To be honest, my Frisk Week penetration craving had been pretty much sated by the three orgasms earlier…but I wanted to get my first sex with a new person in three years over with so I said yes.
I started out on top of him and jeez, at first I could barely feel his penis inside me. I’m so used to being uncomfortably filled to capacity by Minx that I guess anything less feels kind of foreign. But I slowly adjusted to the feeing of The Pedant’s cock and – like when you come in from a bright summer day into a dim basement and everything looks pitch black for a minute – what had initially seemed like blankness started to slowly take form. I think The Pedant’s package does indeed qualify as “small” and that I might ideally like something just a touch bigger, but it was still pleasurable and I can’t tell you how good it was to be able to fuck him as hard and fast as I wanted without being shivved in the cervix. I did worry a little that if I wasn’t feeling him too much, maybe he wasn’t feeling me either – but all evidence points to me having a really unusually tight vagina, so even if he didn’t find my insides terribly stimulating he probably has the same experience or worse with anyone else.
Oh, but here’s one of my curiosities confirmed: apparently I still start feeling chafed pretty fast, even with a small-to-normal cock. WTF? I really want to try non-latex condoms sometime and see if they’re any better. Although The Pedant apparently felt the rubbing, too, and volunteered to pull out and re-lube, so maybe it’s not a latex sensitivity that’s plaguing me.
Anyhoo, when I think back on the sex and kind of run my internal videotape in fast-forward, it’s hilariously spastic and varied – like I said, I started out on top of him…but then I got bored and wanted him on top (where I brushed his nipples with my thumbs and whispered in his ear that I wanted to feel him come and he gasped and thrust harder but did not orgasm) and when it became obvious that I couldn’t wank effectively with him on top of me and he wasn’t going to come any time soon, I had us switch to doggie style so I could haul out my vibrator and maybe get a good Frisk Week payoff that way. The Pedant indicated that he probably wouldn’t be able to come at all since he’d orgasmed earlier in the evening; at that particular moment it sounded like a good thing to me. I could focus on my own orgasm and not worry about The Pedant beating me to the punch.
Sadly, neither of our bodies was cooperating; I was too sensitive from my previous orgasms and The Pedant – after ten minutes or so – told me that he was too “spent” to really make things work (I did notice his erection seemed a little bendy and he’d sometimes surreptitiously pull out and jerk off for a minute). I was like “Ah well…it was a nice try!” (still on my hands and knees, face in the pillow) when suddenly I was experiencing a much more distinct and targeted g-spot stimulation and realized that, rather than giving up entirely, The Pedant had withdrawn his penis and replaced it with a couple of fingers. And BOY HOWDY did that get my motor revving! I settled into a more comfortable position on my back and got myself off twice in a row with my vibrator while The Pedant gently and skillfully fluttered his fingers inside me. And then after a few minutes of cuddling he started caressing me between the legs some more, but there was just no way in the world I’d be able to come again at that point (or if I did it would probably hurt) so I definitely told him I was done orgasming for the night.
More snuggling ensued, and even when The Pedant finally decided to get up and start looking for his clothes, he frequently got sidetracked running his hands over me some more. To be honest I think I was kind of biding my time for a while there (like since I had those first two orgasms and he had his one…), wanting him to leave so I could process everything that had happened…but the novelty of him being so puppy-snuggly was interesting, and I didn’t hate him being there, so I let him stay out of sheer curiosity to see how long he’d keep hanging around and how long he’d keep touching and snuggling me. I would be open to him sleeping over sometime; based on what I’ve seen tonight, I think we’d sleep really well together. But last night I hadn’t been expecting more than a few hours’ company so if he’d declared an intention of staying over I definitely would’ve made some excuse why it wasn’t feasible.
Even when I walked him down to the building’s front door to say goodbye, he seemed loathe to stop kissing me – it was very sweet. But eventually he did indeed leave, and I started writing this blog post that ended up being so long and rambling that I’m only finishing it the next day.
tl;dr: had sexytimes with The Pedant that included (but didn’t focus on) intercourse. It was fun. Came five times. Fully intend on repeating the experience.
*The time of month when my hormones turn me into a giant horndog with a ridiculously strong need to be penetrated.