Boy Hole

You'd never believe the story of how I fucked a guy for the first time. He was a drinking buddy, nearly twice my age and a head taller than me.

I didn't know I was even interested until I transitioned from female to male. Suddenly I felt the dick and the drive that I had been missing all my life. The hormone therapy, testosterone, made me as horny as a teenager and I needed to get off with someone. As it turned out, my silver fox buddy needed something from me too.

The seduction started innocently enough over a couple of beers. He was telling me about work troubles, family troubles, and then, as usual, once he was midway through his second bottle, he told me what was really on his mind: he had an upcoming appointment to see the proctologist and he was scared shitless, so to speak. He was afraid of cancer, sure, but mostly he was anxious about someone probing his ass. He'd avoided this sort of appointment up until now, but at his age, it wasn't safe to keep putting it off.

I've been through my share of anxieties about penetration. I'm a trans guy with a "bonus hole" for god sakes. But I never understood why some straight guys are so afraid of getting their ass felt up, especially when they have the fortune of sexual arousal from their prostate. Hell, I love anal penetration, and I don't even have that sweet spot. I guess I never worry too much about being emasculated, being born with a female body steels you against those worries by making your worst fear true from birth.

So anyway, being the kind of friend I am, I decided to air my critique of uptight straight dudes and then probe him further:

"What's the deal with straight guys worrying about their precious asses?"

He fires back defensive, "I'm not worried about being seen as feminine. And I'm not a homophobe."

"So then what?" I challenge.

"I just get really freaked out if someone tries to touch my ass!" He replies, vexed by having to spell out the obvious.

"Like at all?" I ask.

"I've never had gay sex," he replies, as if that helps explain anything.

I push, "I know. You've told me that. But... I mean, hasn't your wife ever just slipped in a finger?"

His ears get red at my asking such a personal question, "No! Never! We don't have sex like that."

He falls silent. I sense an opportunity in his willingness to dwell in the discomfort of this conversation, "Hmm...Do you ever think about it though?"

"I dunno. I don't like to really. It makes me feel weird. I'm curious, a little...." He says while looking down, as if he's ashamed to admit it.

I soften my approach a bit, recognizing his shame like it's my own. "Did someone try to touch you, or make you feel wrong about it?"

He pauses for so long I think I've crossed a line from playfully teasing him about his ass fears into something far too serious and painful. I try to change the subject but my mind goes blank.

He fills the silence with confession, "There was this one thing, when I was kid. I dunno. It was weird. I dunno how to describe it. It was this friend of my father's, a drinking buddy. He'd come over on Saturday mornings and they'd start drinking early. My dad would pass out or just zone out to the TV and his friend would come up to my room. He took a lot of interest in me; he would ask me all about my model planes and play with me. But then sometimes, not everytime, but sometimes I would pull my pants down and show him my butt."

His face is burning red as he pieces this story together. "I don't know why I did that; or what was wrong with me. He just took an interest in me and I went and did such a stupid dirty thing."

Fuck. I think I know where he's coming from. And that it wasn't his fault, but telling him that probably doesn't help. "How did he react when you did that?"

He pauses again, scrunching up the edges of his eyes and contracting his temples, like he's digging the images and feelings up from a deep corner of his mind. "I guess sometimes he would ask me to do it...and sometimes he would feel it a little."

"Did you like it when he would feel it?"

His voice cracks and pitches up to become almost child-like, "I'd ask him to rub it and to tickle me. I started getting woodies so he stopped coming to my room. I was bad and messed everything up."

He stops short and his voice drops back to its normal low rumble. "Ugh, what am I talking about?" he beats on his temples with his fists as he snaps back to the moment.

"It's ok" I say softly, putting a firm hand on his shoulder. "You're ok now."

I give him some time to collect himself by heading to the fridge to grab us two more cold ones. I snap his open for him and toast, "to letting out all the fucked up memories sick fucks gave us." He smiles and relaxes back against the couch knowing I'm not going to make fun of him, pretend he never said it, or be freaked out by what he was telling me.

I shift the conversation to other things, to football, to the most recent restaurants we ate at, to the science of genes and trauma. My traumas left me with a disposition for stubbornly persisting toward what I want, so I circle back to his anxieties about his ass. I tell him there's this approach to healing trauma where you revisit the event in a controlled environment with someone you trust. For example, the proctologist is a controlled environment, and I suggest he could note the feelings that come up, maybe write them down. I expect to get smacked down hard for this touchy feely suggestion. (And honestly, I provoke him because I enjoy his smack downs.)

But this time he surprises me. "What's the fun in that?" he asks with a glint in his eye.

"Well, I could walk through it with you first, break out the rubber gloves." I intend to laugh like I'm making an offhand joke, but it comes out pinched from my own excitement at the possibility.

He just looks at me hard, holding my gaze until I drop mine.

"What do you want to do?" I ask him while looking away. "I could pretend like I'm your dad's friend, or you could be him and I could be you."

I fill in his silence, "Or I could be the proctologist," I add with that same stupid nervous laugh I wish I could just squelch.

"You decide," he commands, clearly wanting to cede responsibility in this situation.

He's super tense. It would be strange to try to kiss him or be affectionate since we don't usually interact that way. Instead I start stroking his cock through his jeans. His breath is hot and hoppy on my cheek.

I stop for a moment, look him in the eyes, serious. "If you need me to slow down, say yellow, if you need me to stop say red, ok?"

"OK" he breathes.

"Why don't you stand up and walk over to the TV, I want to watch you walk."

He obeys and walks slowly. He's tall and slim and his ass is tiny, even under his tight jeans. I can hardly see anything. I tell him so. "Why don't you pull down your jeans a little for me?" I hear the pop of his button and the unzipping of his fly before he hitches them down from over his whitey tighties. "That's really nice. I like that. Stick it out, put your arms down on the TV stand. Arch your back." He obeys and I am starting to appreciate the view of his tight ass. Even though he's my friend I'm seeing him in a totally new way. His vulnerability is such a turn on.

"Pull down your underwear." He freezes. But he knows his safe words; he's playing. "Did you hear what I wanted? I want you to pull down your underwear so I can see your bum."

"I don't want to" he pouts, but still standing in the position I've orchestrated.

"Come on, please? Please let me take just a little look."

"You have to tickle me first."

"Oh, I see you need to be tickled. I don't know where you are ticklish so we're going to have some fun figuring that out."

I walk up behind him and brush my (always) hard cock up against his ass before descending my fingers all over his belly, hips, and thighs. He's writhing in pleasure at my touch, squirming and holding his arms in close to his body as if they could offer some protection that way. I get him onto the floor, straddling his boner, but careful not to do more that touch it incidentally as I wrestle him around. My relentless hands move up his torso, into his armpits, and across his throat. He's gasping for air and begging for mercy, but still no safe word, so I work him over until I can't keep myself away from the bulge in his pants. I decide to tackle the issue head on.

I stop and get off of him, he's looking up at me breathless and euphoric. I change my demeanor, "what is this?" I ask him sharply and point at his crotch. His smile fades and he moves into that headspace that I observed earlier. "I, I, I" he starts stammering. "Did you get a woody?" "No" he says softly, looking away from me, and squirming with his arms to try to minimize the tent in his underwear. I slap his hands away and pin him by the wrists to the floor. "Yes you did. I see your big boner right there." I reprimand, pointing. "Did you get horny from me tickling you?" I ask sternly in his face. He turns his cheek toward me and I grab his face. "Look at me when I'm talking to you! You are such a dirty boy, letting your dick get all hard like that. You shouldn't be getting turned on by another man tickling you. That's wrong. You should be ashamed of yourself." I find myself in a state of flow, on some other plane of ecstasy spouting shame at him.

"You need to be punished. A real man requires discipline so that he doesn't pop a boner over every little thing, especially over rough housing with his buddies. Stand up and strip."

He does as I tell him, and I breathe in sharply as his cock pops out. I fight the urge to suck him off and end the scene we've created together. I have too much work to do on this man's scared horny ass.

He catches me staring and he starts chuckling softly. I mouth the words, out of the role I'm playing, "you are so fucking hung, I want you." To which he starts grinning from ear to ear. We are about to lose it as I walk over to him and bend him over the arm of the couch. "Stay here and don't move."

I quickly grab any butt toy I can find in my own drawers along with an assortment of household items that could double as anal toys, Q-tips, drum sticks, an espresso tamper, a cucumber. And a full jar of coconut oil from the kitchen. When I come back he's changed position as if he has no qualms about what I'm about to stick up his ass. He's kneeling, legs spread wide, on the seat of the couch, his ass perfectly available.

I lay out all the toys and objects in front of him so he can see what he's in for. I have no shortage of my own toys, soft beads, vibrating beads, machined steel rods, a dildos in various sizes, not to mention the 7 inch prosthetic dick I'm packing.

He inventories the array of pleasures that await his little hole. He's especially drawn to the steel, running the cold smooth surfaces across his fingers. He breaks character to tell me, "I'm a little nervous about all this." I respond by running my finger-tips down his bare back and across his ass, telling him what an amazing ass he has and how much I want to tickle and fondle it.

I pick up the q-tips and dip them into the coconut oil before spreading his cheeks open. "This won't hurt a bit, I promise." I assure him, slipping away from creepy uncle mode into doctor mode. I brush his sphincter with the oil and watch as it dilates and closes rapidly. I never knew I could be so turned on by the functions of a man's ass; it's like an eye. I decide not to let the coconut oil go to waste and I lick it all off of him, slipping my rigid tongue into his hole every now and then. At this, my vulnerability, he relaxes his back and starts groaning in pleasure. I pull out to ask him, "oh you like that do you? Let me show you what you've been missing." I dive my tongue back into him and start to play with his balls.

I come up for air, pressing my body into his, and my cock firmly onto the crack of his ass. I want him to know how hard he's making me. I whisper in his ear, "which of these items do you want me to wiggle into your ass first? And which one do you want inside you as you come?" He picks up the vibrating beads and then pushes back against my cock. I practically grab the beads from him, give them some extra lube and start popping them in one at a time, taking my own pleasure in the ways he relaxes and contracts at each little tug and push.

I love the low rumble of his voice as he moans with his mouth closed. He's hanging on the edge, his cock pressing into the leather couch, his balls swelling with come. Once I get all the beads in I wiggle them with my hand and he lets out a yelp. "I've got you now, boy" I tease. I pull them out rapidly and he lets out a guttural sound and breathes heavily. I work my way through all the soft toys, waiting until he's open and pushing back on a small dildo before moving on to the steel. I remember reading somewhere the steel rod was for prostate training, so I stick with the training theme.

I ask him to hand me the steel toy, shaped like a rod with a penis tip and several balls spaced a few centimeters apart. It's cold so I warm it up by giving it a good rub with coconut oil. "Press back onto it," I coax him. He's being so good. And for someone who started out scared out of his mind, he seems to be very much enjoying himself. He takes it quickly, deep into his ass. His moans turn nearly to screams as the heavy tip probes his prostate. "You like this?" I tease. "Yes" he yells, "Fuck yes." I start using my hand to vibrate the rod in small circles and stimulate him deep inside. He's yelling more, but he's become unintelligible. I stop moving and tell him to be still, a command at which he seems to collapse into a whimper. "Stand up" I tell him. His leg has fallen asleep and it takes us a few seconds to shake out and get back to where we were.

"Ok boy, I told you, you needed discipline. I need you to stand here and hold this in your ass for me. Squeeze it in while I'm sucking you off and do not come." He's struggling in the space between wanting to continue and wanting to let it go. I take him into my mouth slowly, agonizing over each stroke of my tongue, playing with the sticky precum that's oozing from the head. We are both enraptured by his cock.

I stop and fall back and just watch him struggle with the sensations in his sex. "You are so fucking hot; so beautiful." As I praise him, I see his eyes welling a bit. "Come with me," I say as I take him by the hand to the bedroom.

Once we reach the bed I slide the steel out of him. When I roll him onto his back I'm surprised how pliable he is, given that he's usually wound so tight. He looks blissful and eager to please me. I take the chance, "can I fuck you a little?" He groans in anticipation, asking, "what are you waiting for?"

I pull myself out though the ring of my boxer harness and slip on a condom with a heavy helping of lube. I feel nervous and incompetent as I do this for the first time, but he's grinning at me anyhow. I slip it in and he takes me easily after all his hard work and preparation. I can feel the tightness of his grip on my shaft and my hips are bucking as if I could shove my small fleshy dick all the way up to his prostate. The inside of my dick rubs against my sex with every thrust, encouraging me to go deep and hard. We wrangle his legs around my chest and I pound into him. He's gripping the mattress with both hands as I nail him to it.

I back off a little from sheer exhaustion and start stroking his cock. I move inside him in little playful motions, with no need to finish myself and plenty of self control. I want to fuck that sweet come out of his dick. I tell him so, "Shoot it, shoot it all over me, onto my belly." He's making sounds I've never heard out of a man before, his head thrown back, eyes closed. "I'm gonna come," his moan sounding like a plea. I reply, "I'm coming inside of you." And when he shoots it's like he's shot both of our loads. We collapse into a tired wreck of limbs before we wrestle and tickle each other all over again.