The Simple Pleasure Of Pillows

Mid-20s, and … still a virgin, I was in a nice hotel on business for a couple nights. My first time ever in anything fancier than a Holiday Inn. And first time ever in a king - size bed. I’d never even SEEN a king -size bed before. I was genuinely perplexed. Okay, why? What the heck do even two people do with all that space? It was a waste. Ridiculous!

Just me there that night, I thought it was really pointless. I’d been perfectly content in a twin for over 20 years. By this time I had a full in my apartment but still apparently terminally single, I thought that, too, was pointless. Not like I need all that room to just jerk-off. Even on those occasions when one of female friends would sleep over after a party or just a late night out with friends, she’d never stay on her side of the bed and I‘d wake up with her snuggled against me or halfway on top of me. Not that I minded, but it’s not like we were having sex. Disentangling in the morning was sometime awkward. Pleasantly so, but, still.... We coulda slept like that in a twin.

Anyway, being alone, I decided to be “daring” and sleep naked, which I NEVER did (until a a couple years later when I had my own apartment w/no roommate.) So, I stripped down and slid between the sheets.
 

I had a major, (or so I’d thought) meeting the next day. My first representing the company on a significant Superfund case, nearly seven figures of settlement authority but an admonition not to cough-up anything close to that. So, you could say, yeah, I was a bi tense. Not that I needed that excuse: of course I was going to masturbate, there never had been a question about that. But I'd be lying to say I wasn't expecting and looking forward to the ”stress relief” aspect of it. Honestly, I was afraid I might not be able to sleep without masturbating and orgasming, first.

So, that night, just being in the hotel room on my own hadn’t been the impetus to do myself, as it would become in later years for me and apparently many others. But it had offered an absence of any impediments to my pleasure - no roommate to overhear me all lubed-up and getting excited or to knock on my door before realizing what I was up to or to come with the cordless phone and a call to interrupt me. You have to take such things in stride when living with others and I accepted that if I wanted to do myself, I just had to live with such annoyances and perhaps a little embarrassment. I can't say I wasn't pleased with the prospect of real alone-time.

Nor though, can I say I wasn't conscious of the fact that, unlike my friends, who, given a night in a nice hotel and a big bed, would be looking forward to time with their girlfriends / boyfriends / friends with benefits and having sex with each other, I was looking forward to time alone with no one so I could have sex with myself.

I wasn’t hearing anything from the adjoining rooms, attributing that to the hotel’s 4 Star rating & more substantial, modern construction than the Holiday Inns or Super - 8 level motels where my family had stayed on vacations In years past. So I was reassured that my neighbors were not likely to hear me as I doing my thing. Anyway, I was just going to masturbate, a quiet activity as I wasn't in the habit of vocally announcing my climax to the empty room in which I was pleasuring myself. And what did I care anyway? It's not like anyone there knew me.

This bed, though ridiculously large, was, I must admit, great: nice & firm, the sheets soft like, what… silk? They weren’t of course, but they felt really nice. (Does anyone even really have silk sheets, I wondered?) The pillows were really extra-big too, a bit extra-wide-around and way longer than the “regular” pillows I was used to. Certainly more comfortable to lay my head on than any pillow I'd used before, due to their extra plumpness. And though I’d never been a pillow-humper, I think it was simply their size that gave me the idea to take one of those great big ones under the covers with me.

I don’t remember now whether I did it to just feel what cuddling with it would be like (I knew some people liked to sleep with a “body pillow ”) or to actually use it for a different purpose than that for which it was designed. I‘d never minded having one of my friends pressed up against me in my bed and If she’d noticed on waking my erection pressing into her on a couple of those mornings, she‘d never said anything. And I had, years before, “dry humped” with another friend, clothed, so I think it probably had been the latter, more intentional idea. So, yeah. It’s not like I didn’t know what “pillow humping,“ was. As a teen I’d “done it” often with my sister’s bean-bag chair. But it hadn’t ever occurred to me that a plain-old pillow could work, though I was vaguely aware that girls used them, which made sense to me because, duh … clitoral stimulation. I’d masturbated a lot and had been creative. But I’d never actually humped a pillow.

So I’d gotten nude and grabbed one of those king-size pillows and “taken it to bed.” Whether or not I'd initially intended to get it on with the pillow, I'd quickly wrapped myself around the thing under the sheet, blanker and spread, positioned my half-hard dick in what I thought would be the correct position and proceeded to “hump”. I didn’t really know what I was doing, in the sense of how to “properly“ do it with a pillow. I thought that, for any guy doing himself, employing any technique, there must simply be a ”right way“ to do it. “Right” meaning: 1. It felt good and was fun while you were going at it, and 2. it ultimately would make you cum. I like any other guy, I just had to figure out what that was.

It did take a while for me to get the hang of it; the right pressure / position and initially, it wasn’t doing much for me. With my friend, dry-humping her had been so exciting I had to consciously try NOT to cum. (A girl you’ve been crushing on will do that to you.) Especially when she starts humping back at you and then is suddenly writhing in her own orgasm. (Holy shit, I made her cum!) I’d deliberately kept my dick pointing down in my jeans, afraid I’d orgasm right away if I pointed it toward my stomach and had my underside pressing against her. (And mess myself mightily, and likely fall asleep. Not gonna impress the lady that way!)

And the bean-bag chair back in high school, that had been smooth faux leather and I’d lubed it so it was all wet & slippery. (And back then it didn’t take much to put me over the edge. I’m sure I’d never lasted even 5 minutes rutting away atop that thing.) 

But there in my hotel room that night once I'd humped for a bit and adjusted a couple times, finally getting my dick property positioned to pleasure me, I soon got it mostly figured-out and was thrusting happily against / into the soft cushion & smooth material, trying different positions, rolling from my side to my stomach then onto my back, arms and legs wrapped around that extra - long pillow, making minor adjustments, then beginning to thrust again, finding my enthusiasm for the venture quickly increasing. As I did, I was also becoming increasingly confident of avoiding the only thing potentially more shameful & pathetic than making myself orgasm on my pillow - FAILING to have an orgasm on my pillow! (If any of you have thought of a great & unique way to masturbate only to discover, sometime later, nude, sweaty and maybe sore that it wouldn't work, you get it.)

Level 1: Achieved!

As I lay there hunching on and pumping into the pillow, I was surprised at just how much I liked the feel of the whole thing pressed against me, holding it, hugging it. Having its length pressed against me, together with the thrusting motions I was making seemed to add a whole new dimension to the the experience of doing myself. I wasn’t just stimulating my dick, even the been bag chair, really, had just been about that. This was more akin to dry-humping my friend, at least in terms of position and motion. No, she wasn't with me. That, sadly, had turned out be a one-night stand, (if such can be had without actual intercourse). But here, on the plus side, I was naked and was this time working solely for my own pleasure, and boy... I was felling pleasure! Clinging to thing and driving my hips against it again and again, just felt so unlike any other way I'd masturbated, and so very good, I didn't actually want to cum, just to keep humping and humping and humping and getting the good feelings I was getting.

Stroking the regular way, sure, I could go and go, well... sort-of. I hadn't discovered "edging" at that point. But I could usually make it fifteen or twenty minutes, if I paused a couple times. But the times I'd been IN something, when a teen, usually a lubed baggy between the box-spring & mattress or a couple cushions on the couch, or sliding back & forth inside the neck of a vase, it would feel really great...but it was like two or three minutes of intense pleasure and a quick, hard climax. This was much less intense but I could go and go and go and I was using my whole body, hunching, pumping thrusting. I was definitely wondering how much of what I was feeling was like actual sex.

Was I like "practicing" fucking the pillow, I wondered? I'd like to think I could say I was "making love to it" but that wouldn't be accurate. I was ravishing it.

Unlike thrusting and grinding atop my friend, although I was nude and my penis was free, I wasn't in danger of suddenly losing it and cumming way too soo. I was working at it. Thing was, while the pillow was completely unresponsive (obviously), it wasn't exactly giving it up right away. It was soft and yielding as I'd drive into it and slide back, but whenever I’d start to feel like I was getting somewhere, you know, the proper speed, proper pressure, dick positioned just right, not just feeling good but feeling THAT good - getting that feeling where you know that if you keep going the way you’re going, you’ll make yourself cum - I’d, of course, hump faster and even harder…  But then the pillow would just either give in completely to my probing erection and suddenly offer even less stimulation than I’d previously enjoyed, or the friction coefficient of dick on fluff, I guess, would suddenly be too great and my penis wouldn’t slide but just press against the pillow, unmoving, sometimes suddenly and uncomfortably stopping short as I’d be shoving and thus breaking my rhythm. Then I’d have to sort of adjust my dick, reposition myself and start again back to the gentle hump & grind, my hard penis again beginning its sliding & probing softly into the pillow a bit feeling good and then again, after a while, making me feel like I was going to start that “really good feeling” again.

Damn thing was a tease! WTF?

I was just outright using this pillow like a cheap whore! (What did prostitutes cost, anyway?)

What would housekeeping thing when I was done with it? How am I going to clean it up[?

On the third go-round, rolling back onto my side, I'd been at it maybe 20 minutes by then, I had to throw off the covers because I was getting too hot doing all that humping and pumping and thrusting and grinding under there. Then suddenly the cooler air (you know how your room is way too cold or way too hot, usually?) on my body felt great and I don't know but I'd nestled down with it comfortably pumping away, hugging the pillow tightly, side of my face pressed into the "top" end, my legs clamped tightly around its "bottom" end (something that I'd found, to my surprise, really increased the pleasure I felt in my penis) and I started to feel like that "really good feeling" was coming soon. But I really didn't want to kick it up a notch again: it hadn't worked before and I wasn't keen on the extra exertion but was enjoying the cool air on my bare body (something else I'd never noticed before when masturbating) so I just kept gently humping it. And then that "really good feeling" did start again and I just kept gently pumping and it got more intense and I still kept the steady pace and I was like "oh, geeze, this is so good!" I must have gotten the position/pressure/speed right because shove - in, slide back, shove-n, slide back, yeah... it just kept feeling soooo good. I hugged that pillow, pressed my cheek into it and just humped and humped and humped it seemed, I don't know, five-ten minutes maybe? I was on like this perfect pleasure plateau, didn't want to speed up and maybe cum, also afraid to slow down and maybe lose the wonderful feeling my penis was giving me. I just didn't want it to stop.

Holy shit, I'm in ecstasy with a pillow! I'm MAKING LOVE with a big pillow!

This was another one of those moments, l realized as I continued to hump, like first giving myself a blow job: it's was either incredibly cool ... or completely pathetic. Either way, I wasn't complaining. About this time I also realized that what I was feeling was feeling was that my erection, now almost painfully hard, had apparently formed a perfect grove / channel in the pillow into which I'd been thrusting all this time.

So I thought, that's the thing, that's it! I'd figured it out!

And apparently, I had. Although I hadn't increased my pace or the intensity of my thrusts, I soon felt my orgasm approaching. I was so happy with my new discovery that I didn't mind... I'd never imagined a pillow could male me feel so good. If nothing else, that was cool. I kept my pace steady and just let my excitement build. But, geeze, so slowly! I'd thrust forward and Yeah! Then I'd pull back and it's drop back a notch. I'd hunch forward and get that zimg YEAH! Back a notch, then forward ... OH YEEAAH! Back...forward Yeah! (?).... wait, what? Forward...YEAH!!! I made it right to the end on my side, only rolling over atop the pillow to plunge in full-force at the last moment as I felt my orgasm hit and then I got a big surprise. My first spasm was intense and the accompanying ejaculation so copious that the channel my dick had bored into the pillow was suddenly hot, wet and slippery and felt so different and so astonishingly good that I cried out and began thrusting frantically, my whole body now shaking. Then I spasmed and ejaculated again into the warm, wet groove and involuntarily gasped again and again with each jab, feeling like my whole body got "jerked" each time, my glans now completely over-stimulated but me absolutely unwilling to stop my hunching, stop what I was feeling, hugging and squeezing the pillow beneath me as hard as I could as I rode it until the very last quivers of my orgasm, one of the most intense and certainly the longest I'd ever had at that point, finally subsided. I lay atop it, my penis now enveloped in warm and wet, still hugging it for several minutes before rolling off to lie, spread-eagle on my back, still feeling like I needed to catch my breath.

Holy Fuck, that had been good!

How could that have been so good? It's just a pillow!

And I just lay there. Wow, THAT ORGASM... !!!

Thinking about it, I guessed maybe because I'd still been trying to keep up my humping, was why my body had actually been wracked with those shakes during my climax, something that I hadn't experienced before. I'd been in motion - vigorous motion, all of my, not just my hand! - as I'd been cumming. Even when I'd fucked my bed or the couch, when I'd cum, the only thing moving then would be my penis, a little, inside the baggie, my actually thrusting reaching it's peak as I'd lose my concentration and rhythm just before I'd ejaculate and then I'd stop, sometimes flopping down across the bed as I'd cum. But with the pillow, I'd just kept right on fucking. Maybe it was also that the pillow was rubbing against all of me rather than just my penis being physically stimulated? Every other way I'd made myself cum it had just been about my penis, shoved between thighs, sliding in a baggie, caressed by my hand. The rest of me had really had zero to do with it. I didn't have any "erogenous zones" at least, not that I was aware of. Maybe it was simply because humping on the pillow was like dry-humping which was like the same movements as sex, maybe your brain just got tricked or your brain tricked your body and you came like you would if you were really having sex rather than just masturbating?

All of this, too, I though, was maybe why my orgasm had lasted so long. (Ladies, I know: for a guy, a long orgasm is just a question of seconds. But as a guy, and especially a virgin guy, if you are actually cumming for what seems like maybe 30 seconds - which I'd guess is like 3 to 4 times longer than the actual orgasms I'd have when masturbating - well, that's a BIG FUCKING DEAL!)

I got up from the bed, finding myself, oddly, a little wobbly, and headed for the shower, remembering that I would be staying the following night, too.