Questioning
I woke up this morning with a terrible, nasty cold.
That’s what I wrote to my massage provider, with whom I had a session scheduled at 11am.
—I don’t want to pass anything onto you. I really don’t.
I mean, this is not just any massage treatment. The last time she gave me the deluxe nude, she ended up sitting in my lap with her face turning pink as she came all over my stomach. I was surprised, to say the least. I mean, the deluxe nude usually just comes with a lot of hot, smooth bodysliding and a hand job that lasts basically for the entire hour. But during that session she did all of it, everything a boy could desire. All except Greek, anyway. Was she aroused by me, in particular, or was she just aroused?
Maybe I’m her favourite. I didn’t think she liked me that much, but now I’m thinking, maybe.
The first time I went to see her, I asked her to peg me. I hadn’t ever felt it before. I mean, I stick things up my ass all the time when I’m jerking off. I’m not sure how many guys do that — heterosexual guys, I mean.
I got the idea from porn, obviously.
I don’t watch gay porn, I’m not gay, but one time I found this video where a girl (woman, I should say, they don’t like being called girls) was getting railed in different ways by three guys who were each stuffed with a butt plug. You could see the base of the butt plug between each guy’s cheeks, as he penetrated the woman.
Something about it made me pretty hard. I felt myself tighten and grow, then looked down and there it was, my familiar old dick, the usual size if not a little bigger even. Bulging just like when I used to wear tighty whitey underwear in middle school.
It always makes me light up when I get a woody that big and natural these days, if there isn’t a real girl around. (Woman. Sorry.)
They were different colours. The butt plugs, I mean. Well, the men were all different colours too, if that’s important. There was an Asian man, a Black man and a white man. Why do I capitalize those letters for men of colour, but not for white men? Well, honestly it seems like we don’t deserve capitalization, for all we’ve done to those other races. We’ve got to stay lower-case for all the shit we’ve put the world through.
Anyway, I became obsessed with trying to masturbate with an object inserted into my ass. Suddenly I felt an emptiness where I’d never even thought of it before. I began to wonder what women feel like with that cavity inside them all the time. Are they always waiting to be filled? Do they feel empty and collapsed?
I’ve never felt it before, but I started noticing a concavity inside my pelvic space. I would tighten my muscles, bringing them up toward my belly button, and a large craving would subsume me. And I wanted, finally, for the first time in my life, to feel penetrated.
Does this make me gay?
I started off small.
I didn’t want anyone to think anything suspect, so I entered the sex shop on the pretext of buying my girlfriend a relatively vanilla sex toy. The shop had a side door and a main door, and I sat in my car for about ten minutes deliberating which one to use.
Should I walk confidently through the main door as if stopping at the corner store for a bottle of kombucha? It would show that I didn’t care. It would show that I hadn’t been obsessing for two weeks about what it feels like to have an oblong object inside you when you come.
But if I did that, my acquaintances in this uncomfortably small city might see me going in, and think that I was a gay boy obsessed with butt plugs and things.
—After all, they’d think to themselves (and probably say to one another), He’s been single for several years. How long’s it been since you saw him with a girl? Oh, awhile. Seems like he’s finally admitting his preferences. What took him so long? And that kind of thing.
I opted for the side door, and entered confidently. The store appeared just like a candy shop, very yellow and bright, dazzling my eyes. I sort of shook my head, like I was shaking rain off my hair. But really I was getting oriented to the brightness and the rows of dildos hanging there for everyone to see and touch and think about putting in themselves. A rainbow of shiny negligees hanging in rows, like a lineup of headless female sex robots.
Along the outer walls, lime green shelves housed every size and shape of sex toy. A whole alcove was dedicated to silicone half bodies and full bodies, good for when you’re really lonely. (I’ve definitely never tried one of those, and I wouldn’t lie about that. I mean, why would I lie?) I’m not that desperate.
I pretended I didn’t know what I wanted.
—Just a little something, something to spice things up, I said confidently, as if I knew what spicy feels like. I can’t even eat hot sauce or my acid reflux will act up. The last time I had unpaid sex was three years ago in a relationship that only lasted for three sex acts. Three seems to be my magic number.
—Here’s a set of three butt plugs of varying sizes, chirped the beautiful sales girl.
She wore her long dark hair in undulating curls down her slender shoulders, a purple push-up bra under a pink sheer blouse, dark Brazilian jeans (the kind that push up a girl’s bum) and white wedge heels with silver accents.
Her nails were as pink as her lips. They tapped their owner’s enthusiasm on the plastic package, landing right on the middle-sized butt plug. That was exactly the size I’d been dreaming about.
Her finger touched it again and again on the tip. Tap, tap. Tap-tap-tap.
So that’s how it would feel rubbing against my prostate, just like her finger, like that. I didn’t look down because I didn’t want to attract any attention toward the moving front of my pants as my sex organ stood up hard and purple thinking about the thinness of the plastic barrier between her fingertip and the medium-sized butt plug. Tap-tap-tap. I just shifted my stance a little and flicked my eyes briefly to her cleavage and back to her face.
I don’t think I’m gay.
—I’ll take it, I told her.
What: you want to hear the rest?
Well, there isn’t much to tell. I got sick and couldn’t attend my last appointment. I really hope my massage provider won’t hold it against me; but then, probably not, since she likes me so much.
As soon as this cold clears up, I’ll text her again. I can’t stop thinking about her, of course I’ll text her again. Those mesmerizing eyes, yes, the way she looks at you, but more than that, more than that. Actually I like her lips best. I’ll bet she doesn’t get that compliment as much as the eyes thing. Probably every single one she sees — I love thinking about that, the lineups of men she takes, every day — all of them say, I love your eyes.
Actually it’s her lips I fantasize about. They’re shaped just like a cupid’s bow, simple and curved and medium-thin. Not pouty. Perfectly defined. Often they break into a smile that looks like a delicious slice of apple, juicy and raw, just cut, the edges thin and red. Something crispy that you want to eat.
And when she comes close and kisses you, the lips become blurry and soft, just soft enough, wet. She eats your mouth. I mean, I don’t know if she does this to everyone. She eats my mouth. Dominates my tongue with her tongue, probing my mouth with her soft pink lips and tongue. Then she plants kisses, one after another, all the way down my chest, stopping at my nipples.
—I love your nipples, she says.
Is it weird that nipples turn me on so much? I mean, not just a woman’s nipples, but my own, too. They used to have zero sensation. Then I watched a porno of some hairy-chested guy who had three girls working on him all at once. (Sorry, three women.) He was Black. The women were white, they don’t get a capital either. A brunette, a blonde and a redhead, of course — the trifecta.
The redhead licked his loins with a long glistening tongue until she took his thing in her mouth and started bobbing her curly head up and down, up, down (way too fast in my opinion), while the blonde sat on his face gyrating and writhing. You could tell she was faking it. The brunette, though, she suckled on one of the guy’s dark Black nipples, poking her tongue into it and pushing it, then batting it fast, then circling it very slowly, then drawing it into her mouth to suck it again.
I had to unbutton my jeans, I was captivated.
And besides the suckling action on his nipple, one of her hands worked the other nipple, pushing and pulling it between her thumb and fingers. You could see how big it made his erection, it would throb and spill out of the redhead’s mouth just as the brunette twirled her tongue fast around the nipple, then sucked it into her mouth.
Just talking about this I’m going to have to unbutton my jeans again.
Is that weird?
Yes, I’ll admit it.
After that porno I started doing the same thing to my own nipples while I jerked off. Just plucking them with my fingers, pushing them in like a button, pulling them out and even pinching them a little. I imagine that a girl is doing it. I mean, I imagine a woman doing it with her lips and tongue, while I hold my dick and squeeze it first gently and then harder and then gently again.
It kept me very satiated for a long while to learn that trick. There was something breezier and more expansive about the nipple pleasure, dare I say energetic? It made me feel like my skin was swelling up with moisture and leaking desire out a million invisible pores, but never getting close to the geyser of orgasm. Swelling up like tears in eyeballs, but never crying.
I don’t cry much at all, does any man?
After several weeks of exploring nipple play, it still worked, but I became accustomed to the pleasure. I held the trick and played its edge, until the pure crazy novelty subsided. I got that common human urge for something more and it brought me to the internet, of course. That’s how I found the butt plug video. Three different-coloured men with three different-coloured butt plugs.
Now three different-sized butt plugs lurked in a plain bag clutched by my sweaty fist as I headed out to my car. I left through the main door because I didn’t want the sales-girl to think I had anything to hide. I was just buying something special for my girlfriend, after all. (Sorry: sales-woman, woman-friend.)
I tried all three sizes as soon as I got home. I didn’t want to watch the original video that intrigued me, I’d become too accustomed to it. Instead, I watched one of those pornos for girls that’s full of soft, smooth couple sex — lovemaking. Nice slow sexy music in the background. A white bed. In these videos, she gets to come every time. He gives her lots of deep, slow oral between her open legs, until her head flips to one side and then the other, and her hips buck toward his face while his tongue keeps licking and plunging into her. Then he gets on top and starts sliding into her wet, satisfied cunt. She moans and clutches his back as he keeps thrusting and we imagine her coming again and again, even though her clit is not being stimulated much at all.
I watched that kind of porno because I wanted to imagine I was him, except with a butt plug penetrating his ass.
Penetrating my ass.
I did it.
It was a little difficult the first time, lubing it up, easing it in. It took quite awhile. I had to do some deep breathing. I just kept watching that couple making love, his long hard penis filling her up in all those positions: on her back with her knees up near her ears, her mouth making a tiny little O as she says exactly that, O, each time he thrusts into her, and then her face is muffled into the white pillow once he flips her over and starts stroking her from behind.
At that point, the plug was fully inserted in my ass. I held my dick and it grew enormous as a sudden spasm of pleasure gripped my insides. Yes, my insides. I felt full, I felt wrapped around an exquisite hardness, a proper phallus.
I felt the tip of the sales-lady’s finger rubbing at some amazing spot I never knew existed inside me.
A lightning bolt of relaxing, orgasmic sensation blasted straight from my ass to the top of my scalp, riding my skin with waves and tingles on the way back down my spine. Another lightning bolt as I pushed it a little deeper.
So this is what she feels, I thought, and moved my hips just slightly to enhance the sensation. My eyeballs grew hot, filled with tears, of course I didn’t cry or anything. I just kept rocking my hips and feeling that special rub on my insides, feeling at one with all woman-kind.
Without even looking at the couple making love, I burst into the longest orgasm of my life. A right mess.
I know, right? It’s been pretty rare that I’ve jerked off without the butt plug ever since. I got better and better at inserting it, now it just slides right in. I open to it, just like a woman. I let myself soften for it.
But that doesn’t make me gay. I certainly didn’t feel gay when I asked my massage provider to peg me the first time I saw her.
She wore a black fishnet body stocking with an opening right at the crotch.
I could see her vulva with its tiny triangle of dark hair. She massaged me with hot oil for about a half hour, rubbing her body along my own, and I could feel that warm moist crotch whenever it touched my calf, or my lower back.
Then she murmured, I’ll be right back, and after a couple minutes she turned me on my back facing up. There she was, standing with a strap-on aimed right at me. The dildo was (thankfully) rather small and light brown.
After that, it’s all a blur. The only thing I can remember is holding on for dear life as she railed me, her hair hanging down in my face. She kept saying things like, Such a sweet boy, and You’re so good. I looked up at her eyes, her smeared lips, I was melted. I don’t know how long it lasted, maybe fifteen minutes in real life? Several months, in my fantasy world.
Maybe I’ll ask her to do it again, this time. I mean, next time. This was supposed to be the next time, but I got sick.
I mean, I told her I got sick.
Of course I’m not going to tell her I was warming up by watching a porno about a massage client getting ass-fucked by a naked girl covered in oil. (Naked woman, sorry. )
Just getting in the mood, that’s all.
I watched as the massage progressed from light therapeutic rubbing all over his legs, back and arms, to more daring touches where her hands wander close to his loins and slide over his belly. Then she slides both hands dangerously close to his thing, and it rises hot and pink to salute her. Pretty soon she grips it with all of her fingers, closing round it and squeezing it. First gently. Then, firmer, sliding up and down.
I did the same to mine, picturing how it would feel later that morning to have my actual massage.
The girl (woman, sorry) in the porno moved her hands to the base of the big throbbing dick and then her lips popped over the top. Her tongue swirled around the tip, again and again.
I felt a strong surge, bit my lip to stave it off. Failed. It was coming, it was coming, all I could do was jerk it a little and everything spilled over, too soon. I got too close to the edge of the pool, as they say. Now I was swimming in pleasure.
Everything caved in, I realized of course there was no point in going to my appointment. The thrill was gone, anticipation wasted.
She was understanding. That’s what she said, at least.
—I woke up with a cold, I texted.
—Thanks for letting me know, she texted back, I understand.
Later that morning I did watch the massage video again, this time using the larger butt plug. I focused mostly on the woman’s mouth forming that little O, O, O, until another spurt exited my swollen sex organ. I felt the cavity inside me grow softer and hotter, wanting more.
But I’m definitely not gay.
Amazing ! makes me want to do this with you . I've been enjoying my butthole with my finger , and have thought of getting a prostate massager . So this story is very apropos , and hot !