Dear Straight Men Ch. 02

"I'm an average guy. Average height, average build. I'm strong, but not jacked. My hips and belly are a little thicker than they used to be. I wear my hair and my beard short. I don't shave my body, but I do trim.

"My cock isn't huge, but it's decent--a thick 7.5 inches, uncut. I get hard at the drop of a hat, I stay that way for a long time, and I'm good for multiple rounds. If you're curious about that sort of thing.

"I wear androgynous clothing. Cut-off shorts, cut-off t-shirts, cut-off everything. I don't wear dresses or stockings or things like that, but it's been a long time since I bought anything from the men's section.

"I like my body. I like the way it feels in these clothes. I like going outside and feeling the warm sun on my belly and my thighs. I like the breeze.

"I also like the confusion on people's faces, that brief moment when they don't have themselves all figured out. I like knowing that straight men wonder, however briefly, what I'd be like in bed."

- From "Dear Straight Men"

DEAR STRAIGHT MEN 2: WHAT EVERY BOTTOM MUST KNOW

So you're a straight man and you aim to stay that way.

I get it. Everyone has to have the car, the house, the hot wife, the little soccer players. That's one of the rules about being straight: nobody rocks the boat, everybody gets to brag come Thanksgiving time.

But you don't have everything you want. And the longer you go on like this, one of the things you're not getting seems bigger by the day.

It starts small. You go online, private mode, and you read articles. Not with any serious intentions--just to enjoy the fantasy. Something to get you revved up and masturbate about later in the shower.

You search "how gay men have sex." You get results about cruising, online services, sexual practices, sex positions. "Am I bisexual?" You take endless quizzes, most of them carbon copies of each other.

One day, you do something brave, foolish, wonderful, stupid. You sign up for a website, not under your own name, and you send out a few messages. Again, not with serious intentions. Just for the fantasy.

One of the people who receives a message from you is me.

We strike up a correspondence, just casual at first, but we're soon telling each other things we've barely told anyone, or that we've told no one. I'll never repeat anything you've said. Your secrets are safe.

That's an important rule. If you're a straight guy who wants to get dicked down, stick with guys who know how to keep their mouths shut. To keep it on the downlow, as we used to say back in the day.

Here's what I tell you about me.

In school, when boys would have crushes on girls, I would play along. I wouldn't understand, but I would play along. But there were boys I had crushes on, those precocious feelings of closeness and longing.

I first had sex in college, with a woman. She was five years older, small, but very butch. Deep voice, shaved head, lots of tattoos. She had a kid, a husband. They were getting divorced, she explained to me.

My early sexual history was littered with women with masculine looks, masculine builds, small breasts, wide shoulders, short hair or no hair at all. Some of them have since come out as various flavors of LGBTQ.

I suppose that's another rule. The first person you have to keep your secrets from is yourself. At the time, I would have never considered sex with anyone who wasn't a normatively bodied cisgender woman.

The full all-you-can-eat buffet of my desires was buried. Out of sight, out of mind. And my feelings towards women were loving, but of a possessive, jealous kind. I was easily wounded. I was straight.

Does any of this sound familiar?

Your correspondence with me gets spicy at times. There's no sexting, but there's definitely an unspoken fantasy of us meeting, what would happen, based on my openness about how I like to bottom for other men.

Then, buried deep in the wall of messages, you make a throwaway remark about bottoming. You're curious, you say, you've had fantasies about doing it. Then you immediately move on to some other randy thing.

There's another rule. If there's something you want, something you need, a desire deep down, unfulfilled, you have to act like you don't care. Be so inconspicuous that it's impossible for me to overlook.

I offer you nothing specific at the time, but I explain that I'm vers, explain to you what that means, and I also make sure the tone of the conversation shifts towards us making our meeting a reality.

And so we do. We set a time, I book a place. Nothing fancy, just somewhere where they charge by the hour and mind their own business. I've brought a lot of guys there, including to this particular room.

If you have any uncertainty, you keep it to yourself, but I know this must feel like a whirlwind for you. There's another rule in that, for the straight guy who wants to try bottoming for the first time:

Keep your feet on the ground. Focus on the moment, on your feelings, your pleasure, and don't get wrapped up in what this means for your life. I'm telling you this from experience. It's better this way.

There are some more rules, practical ones, which I give you in advance, along with an apology for how businesslike it is. I promise you, do these enough times and they'll become charged with eroticism.

Get tested. You can decide when the time comes if you want me to use a condom or not, but nothing beats a clean bill of health for peace of mind.

Give yourself an enema. I've sent you an article about it, and a list of places to buy the stuff. It might feel weird, but, honestly, putting anything in your ass feels weird if you're not used to it.

Shower beforehand! I would love to shower with you and make sure we scrub you to a spit shine, but we might not get to that. For both our sakes, wash up. Really get in there, make sure you're squeaky clean.

This is more of a strong suggestion than a rule, but you should plug yourself beforehand. Go to a sex shop, buy a butt plug--better yet, a graduated set of them--and some lube. I've sent a list. Come plugged.

The last rule, for now, is that there's going to be a little voice in your head, giving you a thousand reasons not to go through with this. Don't listen to it. Charge ahead, throw caution to the wind.

When the evening comes, I get there before you do. I prepare the bedside table--baby wipes, condoms, gloves, toys including a prostate massager, butt plugs, a wand vibrator. And a pump top bottle of lube.

Another rule: have your setup ready to go beforehand. No one wants to scramble to find the lube when everyone's hard and ready to go.

I hear your quiet knocking. I open the door and find you standing there, framed against the nighttime lamplight of the street outside the motel. Nobody here but us and the gravel and the cars going by.

You look timid, maybe more than you're aware of. But I notice. I'm immmediately hard for you. Maybe you can see it--that upright ridge in the front of my pants. Or maybe you don't. Either way.

Don't worry. There's nothing... ominous about my desire for you. It's just that straight men getting flustered by other men turns me on.

You scurry in. I close the door behind you. I'm sure your eyes instinctively sweep the room, taking it in, and I'm sure you notice the things I've laid out in preparation for your arrival.

I sit down on the edge of the bed and pat the comforter next to me, beckoning you to sit with me.

Judging from the hyper-conscious way you ease onto the bed, I already know the answer to at least one question.

So I ask the next question.

"You're sure you want to try this?"

You say nothing. You're not making a lot of eye contact. I wait, and eventually you speak up.

I lean forward, just enough to stay balanced as I slip my pants and underwear down to my ankles, then I sit back down. My cock, fully erect, stands straight up out of my lap like a marble statue.

Okay, I'll give you a few seconds to stare at it. But only a few.

"I didn't get it out just to show it off," I tell you, half-joking.

First, I try putting you at ease. When that doesn't work, I use the direct approach.

I whisper, "I want you to get on your knees and suck my cock."

Again, you don't move, but your eyes get noticeably bigger.

You slide off the bed, gingerly, mindful of your ass. You get down on the floor, and you kneel between my feet, eye to eye with my pisshole, which peeks angry and red through the soft folds of my foreskin.

I understand your hesitance. Giving another man a blowjob is within reason. But kissing him first? That's gay.

"We both know why we're here," I say quietly. "This is part of it."

You reach up and wrap it in a loose grip. Nothing terrible happens.

"Pull the skin very carefully towards my body," I tell you.

You do as you're told. My foreskin slides back and settles into a thick ring around the crown of my cock, unveiling my glans. Knowing what to do with foreskin is a good skill to have.

"It feels nice to be touched by you," I say, which true.

You're taking an awfully long time, and I'm wondering if you need further encouragement, or even if it's time to call it off for tonight. But then your mouth descends on me, and, like that, I'm in.

It takes a moment. You're kind of like an alien species disembarking on Earth for the first time. But, as the old saying goes: you can't untaste someone's cock, so you might as well suck him off.

Okay. Obviously, your technique is unschooled. And it's filled with all these little theatrical touches you're probably subconsciously mimicking from porn. It looks nice. But it isn't a real, good blowjob.

"I don't want a show," I tell you. "I want you to make me come."

I put my hand on top of your head, stopping you before you bob too far up, pulling away when you bob too far down. I keep your movements in a relatively restricted range that feels especially good on my cock.

I think it has the desired effect. You seem less in your head, more focused on me, on my pleasure. I told you what I want and you seem to be taking it seriously.

"Come on, babe," I whisper to the top of your bobbing head, "suck my cock. Suck... my... cock... You're doing so good. Just keep that rhythm..."

What you're doing now is absolutely working for me. The great bulb at the end of me is slipping back and forth on your curled tongue in short, brisk strokes. The inside of your mouth is soft and tropical.

"I'm gonna come soon," I whisper.

Then, after a moment, I add:

"And you're gonna swallow it."

This, too, is part of it. A rule you'll learn to like.

To your credit, I don't notice you doing of the usual performative straight man hesitation about this. You're too focused, too set on your task to spend time inventing reasons why this is okay.

As your mouth keeps sliding up and down, as I continue climbing towards that long-familiar moment, I keep up a steady stream of whispered instructions, encouraging obscenities, and some gibberish.

The worst thing I can say is that this is one of the better blowjobs I've gotten from a man who barely has any idea what he's doing. I'm close--I want to come, I really do--but I'm stuck here at a plateau.

I decide that this is no longer your problem. I tap you on the head, and, when that doesn't work, I gently push on your forehead, and that's when you lift your head, only as far as my hand makes you.

Here's a rule. Learn what a tap on the head means.

I start to masturbate, immediately going for fast, ferocious strokes, my dickhead positioned close to your mouth. I put my free hand on the back of your head, making sure you stay put.

"Open up," I half-grunt.

Quickly, I get myself the rest of the way--you really did do most of the work, I hope you know--I put the tip of my cock back in your mouth, as though feeding it to you. You close your lips around it.

Then I come, my innards clenching, squirting rope after rope of cum into your mouth. I don't even know if you've tasted it yet, but you certainly feel those percussive strikes on the back of your throat.

It's a struggle for me, but I maintain enough awareness to talk you through the end game. You can't stop, but you do have to slow down, to be more gentle, to match the sudden sensitivity of post-orgasm.

There was so much, so fast, that the nothing that follows feels like a small lifetime. You wait, a little bit longer than necessary, before finally relinquishing me with a spitty slurp that can't be helped.

I pet the back of your head, subtly keeping your face right in front of my fading erection so you can watch its progress.

I don't tell you this--maybe later--but the fact that you're new at this, that this the first blowjob you ever gave, is so hot for me. It more than made up for any lack of technique. It made my orgasm better.

Now, we check.

I lean down, bid you to tilt your head up. Perhaps by instinct, you open your mouth and extend your tongue. Instead of peering inside, I cover your mouth with mine, suck your tongue, a wet, domineering kiss.

You will never forget this moment. You'll never forget me. The feeling of my cock in your mouth, the taste of my cum, the sensation of swallowing it, of raw egg going down your throat, will stay forever.

I know this because I've been there. I've done it many times since, and they were all special. But none of them imprinted themselves on me like the first. And I hope, like me, that this is your first of many.

I withdraw my mouth with a long suckle of your tongue, right down to the tip, and I bring away the vestiges of myself that lingered there, along with a silky dribble of your spit. I swallow it gratefully.

I keep my open mouth close to yours, As soon as I can summon the effort, I say, "I want you to get up and take all of your clothes off."

Are you enthusiastic? Unsure? Are you one foot out the door? Or is it the opposite? In for a penny...

You stand up, and you squirm and you wriggle until you stand naked and resplendent and panhandled before me. I look you up and down, letting you feel my lustful gaze on your bare and vulnerable skin.

"Get on the bed," I say. "Bend over in front of me."

It's a big ask, I know.

But I want to see your bare ass, the backs of your thighs, your balls, your dangling hard-on, your soft skin, your body hair, all of it, laid out like a delicious buffet. And you're going to do it for me.

Once you've assumed the position, I can see the rosy red base of the butt plug you've chosen for the occasion. I recognize which kind it is and silently commend your ambition. It's small, but not that small.

Whether hesitant or eager, your compliance with my every request, my every order, is encouraging. Have you decisively laid down the burdens of straightness? Or are you just too horny right now to care?

I get up and strip off, quickly and efficiently, letting you feel the clothes hit the edge of the bed, then the weight of my body kneeling behind you, out of your eyeline, making you imagine how this looks.

I wonder, what do you think is about to happen?

Is this it? Is this when I get hard again, lube us both up, slide my cock inside you, fulfill the dream you've denied to yourself for so long and satisfy the curiosity you've tried your whole life to shake?

No, it's far too early for that. A cock in your ass now, any cock, let alone mine, would be an experience so unpleasant that it would put you off gay sex forever. We can't have that, especially not now.

Besides, there are other things on the agenda.

I reach out to you. I want you to feel my hands on your buttocks, my thumbs between the cheeks, just above your perineum--that's the stretch between your ass and your balls--and don't you dare pull away.

Do you like that feeling? Strong hands, a man's hands, gripping you, pulling you apart, exposing the most vulnerable part of your body to the light, to the cool air? Does it scare you? Does it excite you?

"I'm going to take the butt plug out," I warn you. "I want you to hold your breath and clench down as hard as you can. On three, you're going to exhale, slowly, and relax your butt as much as you can."

I give you the three count. Then I hear you exhale.

I grip the base and tug, firm, steady, and it starts to come out, your cute little anus bulging out as the widest point of it begins to appear, a spot of color within a ring of clenching, clutching muscles.

This part, I take very slowly.

"Breathe," I whisper.

Soon, the narrow part of it is on its way out. God, how strange, how overwhelming the sensation must be to your unspoiled asshole, silicone gliding free on a layer of lube, your every nerve alight with fire.

Then it's out, and I drop it wherever.

I know this is a lot of new stuff at once. And you're doing such a good job. Each step we take is asking a lot, but I'm confident you'll keep rolling with it.

I contemplate asking if that was the first time you've ever had anything up your ass for pleasure, but I don't bother. I think I know the answer. I know your type.

Instead, I tell you, "Your asshole looks so delicious, I just have to eat it."

For a lot of straight people, the thought of eating ass never enters their minds. Now here you are, naked with another man, bent over in front of him, feeling his hungry eyes on your tingling asshole.

Maybe you're scared of what we're about to do. Maybe not. I decide to give you some encouragement, just in case.

"You're going to have a lot of first dates with a lot of men, and some of them will want you to eat their ass, and some of them will want to eat yours. Soon, eating ass will seem as commonplace as sucking cock."

I get down close behind you, close enough to feel your body heat, to smell you. As freshly cleaned as you are (and I'm grateful, believe me), the scent isn't what you'd think. It's musky, and very sexy.

Have you ever seen your own asshole? Been curious, looked at it with a phone camera, or maybe bent over in front of a friend and had them describe it to you? I spread your cheeks, exposing you to open air.

I have so many words to say about it. The only thing that comes out is "God, you're so hot."

And that's all I can manage, before I dive in. Using my thumbs to keep your cheeks apart, I lay the broad flat of my tongue over it, letting my spit well up on it, before circling you with just the tip of it.

There's lube--a lot of lube; you'll learn after enough assplay that it doesn't take nearly this much--but there's very little else in the way of residue. You did such a good job. I quickly have you cleaned up.

I want you to sit with this feeling. Do you find it pleasurable, or just weird? I'm guessing the latter--I admit, it took me some time to acquire the taste for it--but I'm not letting that slow me down.

Soon, I'm probing you, dead center, and the wetness of my spit, the lessening tightness of your sphincter as you grow accustomed to the sensation, lets the soft tip of my tongue inside you just a little.

You have that sweaty, slightly waxy taste that makes ass such a delicacy. I'm honored by you. Every straight man should be proud to have an asshole so meticulously cleaned and pretty and delicious.

I make more circles, ever-widening, then ever-tightening, going a little deeper each time, and I slurp you, and I suckle you, and I can't be sure, but I think you're shuddering, and I think you get it.

When I finally pull away, the lower cleft of your buttocks is shiny with my saliva.

This may not have been your thing, but it's something you needed to try. And the same goes for what we're about to do next--something I felt weird about the first time. Let's just say it grew on me.

This was one of my most important rules early on. If there's something you crave, or something you're curious about trying, it might not be good the first time. Give it a chance. Give it a few. This is play.