Dear Straight Men Ch. 02

I get down next to you, near your face, low-key letting you smell my breath, letting you know there's nothing to worry about. Then I reach up and put my hand on your ass and lay two fingertips over your anus.

I want you to feel what they feel like, to feel the distinct pressure. But I'm also sizing you up, feeling for how loose you are, how pliant. You still feel clenched, tense... but not that tense.

"I'm gonna put my fingers in your ass," I say.

I leave you for the moment, crawling over to the loose pile of black nitrile gloves and taking two and and snapping them on. I'm not afraid of anything I might find on my fingers, but this is for your comfort.

To quote an icon of the sex industry, "You're going to poop's house, and you can't really get mad if they're home." That's another rule.

I pump a dab or two of lube into the palm of one hand--remember, it doesn't take a lot--and wipe a thick film of it on the fingers of my dominant hand, smearing them up and down, like four little handjobs.

Then I return to you, kneeling behind you, your spit-slick ass in my face. We're at a good angle for fucking, and it occurs to me that my cock is hard again, ready when you are. Don't worry. We're very close.

You've got me so turned on right now.

I can see between your legs, the way your balls have tightened up like a little fist, the way your cock hangs at an angle, hard and twitching with the beating of your heart, that I might not be the only one.

I lay two fingertips, index and middle, flat on your asshole. It's okay if you flinch. Just don't pull away. I put pressure on you and make firm little circles, not pushing in. Just massaging you.

I'm warming you up, I'm lubing you up, I'm also trying to expose you to a few different styles and sensations of anal play. Let this be your playground, your experience, your all-you-can eat sexual buffet.

Another rule, maybe the most important one, in sex, as in life:

Know thyself.

You'll find it's something straight culture would never allow. But I would. A lot of people would.

I'm sure you'll meet them.

"Ready?" I whisper. "One. Two. Three."

I hear you exhale, and your anus relaxes beneath my touch, and your muscles practically reach out and snatch my two fingers nearly up to the first knuckle. I hold there for a moment, delighting in your grip.

Then I wiggle them a little, and I feel the fainest shiver travel through your body, and I push in. You're tight, but I'm gentle, and we get past the first knuckle of two fingers without too much difficulty.

Do you like it? I'm sure you do. This part, I've always enjoyed, that initial bit of fullness, that roller coaster drop that takes your breath away, the touching of nerves, leaving them alive and singing.

We keep going, wiggling, shuddering, pushing, millimeter by millimeter. I think about asking you how you're doing, but I don't you to get back into your head. And besides, you're starting to push back.

Then we're getting close to the next pair of knuckles, and that's where your taut sphincter starts to resist me. There, I hold. I don't start pulling back out, but I hold.

Pay close attention to your body. What it wants, what it needs. Don't get too greedy too quickly, but don't lose courage, either. Follow this rule and you'll be surprised at what your body is capable of.

I listen carefully. All I hear is your heavy, ratcheting breathing and the excited beating of my own heart.

I massage you, making little circles against your front wall, so very close to your prostate. Outside of you, I press my thumb against your perineum, just above the backside of your balls, like a loose pincer.

Start small. Take it slow. Use lube, always. Pause when you need to. Those are rules.

Once you feel noticeably looser and more relaxed, and not one second before that, I test my knuckles against your grip. They slide through easily. From there, my fingers glide all the way in, up to the hilt.

I can imagine how you feel. Can you imagine how I feel?

I wish you could know how wonderful you feel inside. Past the tight musculature hugging me around the base of my fingers, you're so warm, so soft. Under my fingertips, I can feel the ridges of your P-spot.

I hold there, just for a moment, and you say nothing. Wisely, you seem focused on your breathing. A lot of people don't realize how much they hold their breath during sex. Plus, I can guess what you're thinking.

I say, "I'm going to withdraw, just for now, to get more lube. Then I'm going to put another finger in."

Little by little, I pull my way back out, remembering that blazing, nervous feeling from when I first started masturbating with makeshift toys in my ass, like spicy food. I do my best to take it easy on you.

I waddle on my knees to the bedside table. With a baby wipe, I clean the residue from the glove--there's very little, I promise--and lube up again. Then I waddle back and resume my position behind you.

The first time I ever fucked myself with a proper toy, I was mortified when it didn't come out perfectly clean. Years later, I was fucking a guy, and he likewise was mortified that my cock didn't come out clean.

I was seasoned, but it was his first time. (His girlfriend had given him a hall pass for his birthday, I later learned.) I had to reassure him that I found his body smells and his residue sexy, which was true.

Rule number whatever: you can eroticize anything. If it happens during sex, or before sex, if it's something about the way your body looks or something it does, a scent, a substance, learn to let it turn you on.

I touch your anus, just to let you know I'm there. Then I push. It occurs to me that I never made clear that another finger meant in addition to the first two, or that had been two in the first place.

But, by then, you've accepted three fingertips easily, already up to the first knuckle, and my worries are moot.

Your anus is nearly frictionless as I push in, knuckle by knuckle. My cock is bigger around than three fingers, closer to four. (Not to brag. Well, maybe a little.) But, still, I think you might be ready.

I do the pincer thing with your perineum again. My fingers are in you so deep that I have to use my wrist to move them inside you. Your anus, though stretched wide, looks happy and healthy and unharmed.

Look how far we've come. Is it good to know that your body can handle this thing you've been so curious about? Or is having most of a hand up your ass crowding every other thought out of your hazy little head?

I play with your prostate a while, because I enjoy it, that walnut feeling, ridged spongey flesh, and because I know it's pleasurable for you. Your penis bounces whenever I do something good, which is cute.

But we delay the inevitable, don't we?

I tell you, "Okay, I'm going to withdraw again."

I think I hear you make a noise in the back of your throat, which I interpret as a question.

"Yes," I say, "This is it."

I start pulling out again, much more carefully this time. I know it's an overwhelming rush of sensation, just being filled up by something big, but feeling it move inside you literally takes your breath away.

I kneel-waddle again to the bedside table, since that's where the trashcan is. I take the gloves off, letting one of them make a snapping sound, for tradition, and drop them in there with the wipe.

I ask, "Do you want me to use a condom, or do you want to take it raw?"

The choice is yours. I enjoy both, believe me. I've been with partners who feel less... messy with a condom. But some of them like the intimacy of a bare cock. Some of them like being filled with cum.

You search your heart, and you give me your answer.

You stay bent over, probably expecting me to come around behind you again. I get it. Bending over, me kneeling behind you, sliding my cock into your ass while your face is in the mattress, it's very classic.

But this is your first time, and it's better for you to be in control for this one.

I lie down next to you, on my back, my face near yours.

"Straddle me," I tell you. "Pause or stop whenever you need to. It might be easier if you face away from me, just to start."

I don't tell you that it's going to be difficult either way, at least physically.

But being penetrated by a cock is a psychologically powerful thing. Some straight men have an easier time at first if they don't have to look the owner of the cock in the face.

Soon, you're kneeling, knees splayed on either side of mine, facing away from me, your tense butt very close to my upright cock.

I grip my cock, I put the head of it between your slick cheeks, finding the warm pucker of your muscular entrance. After a moment's hesitation, I feel the beginnings of your weight upon me.

"Careful now," I say. "Remember, breathe out slowly, and relax."

Forget what I said earlier. This is the most important rule.

We spend an awful lot of time with our assholes clenched. You have to learn to relax it on command. With time and training, it gets easier.

So hold your breath, clamp down as hard as you can, then--one, two, three--release your grip and exhale. Nice and slow.

As your asshole inches its way down, past the crown of my dickhead, the bunched ring of my foreskin, the first inch or so of me, the feeling of the warm depths of you is exquisite.

I briefly forget myself, forget my role as sage advisor, and out comes the melange of part-instructions, part-obscenities, part-gibberish as you ease your way down with an almost frustrating slowness.

At one point you stop, and I'm pretty sure you're at the limit of what you can handle.

"Ooh, I'm all the way in," I lie.

Of my 7.5 inches, maybe two of them are inside you. It's okay. I know you expected your first time bottoming to be glorious, for you to be a dynamo of dick-taking, for this to be the gay sex of your dreams.

I've never known a man who could take an entire cock without lots of attempts, lots of experience, and a whole lot of training with toys in his off-hours. Don't worry. You'll get there. Just not tonight.

I tell you, "Move your hips forward and back, like you're fucking someone from behind."

With your hips gyrating, my cock is slipping in and out of you by millimeters. I'm guessing this feels overwhelming for you--I'm sure it's hard to focus--but I'm pretty sure you've found your prostate.

This is good. You're learning your body, your capacity for bottoming, on your own terms. What works for you, what doesn't. And, just for now, you're doing so with an active role in your exploration.

For my part, there's a region of my cock that particularly loves being jerked off, especially by the hot death grip of a virgin sphincter. I suppose that theoretically goes for anyone with a penis.

I murmur to you, telling you that it's time to change up. It takes some doing, but, soon, you're off of me, kneeling on the bed next to my legs, facing away from me, shoulders slumped, deep breaths.

I think I know what you want. But I'm not ready to give it to you yet. There's something else I think you might be ready for.

"Lie on your back," I tell you.

Even more than the physical aspect of taking a cock in your ass, there's an emotional and psychological aspect of bottoming that I'm easing you into--an exchange of power that some men find intimidating.

Lie back. Open your legs. Feel another man's weight on top of you. Look up at my face. Feel my breath. Feel my cock as it pushes in. Give up the grip of your anus, the grip of straight masculinity.

Having someone else inside you, especially a body part as laden with meaning as a penis, is a vulnerable, even scary thing. I only truly came to appreciate that the first time I took a cock in this position.

Don't worry. It's just the first two inches again. I know when to be careful.

Watch me. Don't you dare close your eyes. Watch me fuck you, watch yourself getting fucked, the man looming over you between the wide V of your knees, your erect penis dotting my soft, hairy belly.

Once again, we're hitting one of my favorite parts of my cock--side effect of me being so careful with you--and I worry that I won't last much longer. And I still haven't given it to you the way you want it.

After a few minutes, it's time to change up again.

I stop, and I withdraw, and I bid you to kneel down and bend over, to spread your face and chest on the mattress, your beautiful, freshly deflowered asshole winking at me over the secrets we now share.

I'm behind you. I grip my cock, lay the head of it against your anus, which is closed, but warm and malleable now, and sweaty and slick. It practically opens itself and drags me in. I feel how ready you are.

I reach out, grip your ass in both hands, and do my best to make up for the lack of depth by using strong, steady strokes, knowing that the psychology of it matters as much as the sensation of fullness.

It's good, isn't it? Better than you hoped. Better than you imagined, or could imagine. There's nothing quite like it in the world.

You might be crying out. It's hard to tell through my own hissing and moaning. I'm so proud to be here for you, for this. The first moment of the rest of your life. You beautiful, beautiful man.

I only last about three minutes.

Then comes the clenching, the tingling waves in my core, and it's here in our journey, as you're bent over, another man's hard cock coming in your ass, that I'm afraid there's one more very important rule.

You're not actually straight. Nobody is, really.

I slow, and I stop, and, without meaning to, I collapse on top of you, and you ease down, both of our weights, onto the bed, lying beneath me, my body on top, my pulsing, softening cock still inside you.

Straight isn't something you are, but a script you follow, trading the fullness of your being and your desires for the cold comfort of life within a stifiling and hostile in-group that takes more than it gives.

When I finally have the presence of mind, I weakly push off of you, withdrawing my meek, soft, soggy cock and rolling onto my back, and I lie by your side, panting, our bodies covered in the sweat of two men.

Though mine is down for the count, the first thing that occurs to me as I pull myself together is that your cock is still ready to go. So far, I've given you my cock, and I've tried to give you my wisdom.

I have one more thing to give you.

From the bedside table, I take the prostate massager, a silicone gadget that looks like an ornate letter from some obscure alphabet.

After the butt plug, my fingers, my cock, this probably doesn't feel too impressive. The long, narrow bulb of it slips inside you easily. But I know how the curve, the contours are nestled perfectly within.

I take up the wand vibrator, plug it in, bring it over, those shaky, waddling knee-steps as I pad across the comforter, position the head of it on the underside of your cock, which lies against your belly.

Then I turn it on.

It takes a moment to find the right spot--it's on the underside of your cock, around the base of your dickhead, which is more or less where I like it. It works for you, too, doesn't it? I can tell.

I switch from low to high power, massaging you in tight little circles, careful not to stray too far, holding it where it needs to be, and very quickly thereafter you cry out and you come and you come.

Your semen gets on your jaw, on your chest, on your belly, and I watch with delight as the end of the toy in your ass pulses in and out as your anus grips at it frantically, teasing you inside with its tip.

Then it's over. I click the vibrator off, set it aside, then nestle in next to you. I cradle you to me and touch your fluttering belly. You're still too far gone to really notice. That's okay.

Straight men don't know how to masturbate with a vibrator, do they? But you do. This is more knowledge that I gladly give to you--knowledge that, use it or not, will reshape your life forever.

Your body can do the most incredible, amazing things--you can do the most incredible, amazing things--if you let go of what you think is supposed to be true, and learn.

~THE END~