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August 15, 2025

Alex Becker, ‘Emily Takes A Risk’

Okay, here is what I consider the best of my early erotica.

You can probably pick up context here: Alex fucked things up, he’s alone, and he’s trying to not be such a piece of shit. He’s been seeing Emily professionally for a long period of time, and things finally boil over. What follows is…I’ll let you read it.

The idea I had for this scene was straightforward: write trans sex and be fucking normal about it. Don’t fetishize, don’t moralize, don’t treat Emily as an obstacle, don’t frame Alex’s feelings as magnanimous.

These are two people desperately and deeply in love with one another, and my goal in this scene is to illustrate that plainly and brazenly. Every body is worthy of love, reverence, lust. I hope I got that across here.


‘Emily Takes A Risk’

"You’ve earned a free session today, Alex," Emily said.

"Oh?" I responded. "What’s the occasion?"

She shot me a look. "What? You see me every week for three months and you wonder why?"

"I hadn’t heard of any rewards program."

"You’re the first." She grabbed a marker, made a few marks on the paper. "Here."

It said "FREE MASSAGE” in block letters.

"May I redeem this now?"

"No."

***

There was a rustle of fabric, a soft plop of pants falling to the floor. “You’re allowed to want something, Alex,” Emily said, and I dared to lift my head from the face cradle.

“Like me.” She smiled.

Dressed in nothing but her underwear, her skin gleaming against the salt lamp light, her hair down and hanging ever-so-slightly and appealingly limp from sweat, cheeks flush, eyes hungry, mouth open just enough to see her tongue between her teeth.

“Uh.” Yep, that was what I expected to say. After taking her in, her cute little tits bobbing, nips ready to cut diamond, her just-toned-enough stomach flexing with each breath. And down, to the bits—

The bits. The bulging bits, tight against the white fabric that, even in the low light, caught light and shadow just so, incontrovertibly so, beautifully so.

She was already erect.

SHE was ready to go.

I wanted to leap from the table and pin her against the wall, before asking her very respectfully how she wanted to be touched.

Or wrap my hands around her ass and rub my face on that fucking bulge.

Take a handful of her hair, wrench her head back, and kiss her neck, romance-novel style (we would make an absurdly hot cover couple).

But I didn’t. Because beneath the arousal and the need, the one thing that gripped me was fear. The fear of having something I didn’t dictate. Or an event I planned that no one cared about.

Emily touched me first, and I didn’t resist it. Her fingers trailed through my scalp, gave me those good tingles, all the way down, centering on my package. I got up from the table, pushing up to all fours, crawling towards her a little, then putting my feet on the floor, never breaking her touch, feeling a cold begging to snap.

I tried to push the bad shit out of my mind. It was tough.

Like the realization that I’m surrounded by people—at my own party, that I meticulously planned and executed—that don’t care to talk to me, but know my hospitality is easy enough to take. I knew a better man would react differently.

Standing tall and pulling her close, I put my mouth on hers. She tasted of orange juice and scrambled eggs, with a hint of everything bagel.

Heaven, ready in 10 minutes. That’s what Betty said.

Her kiss made me lose my footing, and I fell into the wall. Emily followed me, her lips never leaving mine.

That man wouldn’t be consumed by his own cruel anger and resentment, letting those emotions find new and exciting ways to justify themselves. He wouldn’t be scared of being open—well hey, guess what, that’s not me, so I get to reckon with that, in this immediate moment, in a goddamned fucking dream scenario that is, like, 2 or 3 on my fantasy list.

A better man wouldn’t have let Betty leave like that.

We made our way from the massage room in a tangle of limbs to the bedroom, a mass of kissing and panting, groaning and grinding. She pushed me away when we crossed the threshold, and I fell on my ass at the foot of the bed. And she came at me, straddling me, her powerful legs and hips grinding her bulge into my own rapidly engorging member. We kissed, our tongues meeting, darting across mouths. I moved down her chin, her neck, her sternum. I wanted to keep tasting her, every part the sweat, the flour, sugar, the bitter taste of her massage lotion. My arms encircled her, pulled her body close. She let out a little puff of air, then looked down at me, her breath slowing as the reality of the moment sunk in.

"Hey."

“Hey." She kissed my forehead, pushed a lock of hair behind my ear. "Is this alright? Are you comfortable?” She asked, pulling away a touch. “I want to make sure. Is this cool?”

What the fuck else could I do? "Yes. Please." I wanted her, I needed her. But that fear kept me from losing myself in the moment.

She pushed me down, and was now lying on top of me, planting wet kisses on my chest, taking my nipple in her mouth, sucking and biting. I couldn’t see her face, obscured as it was by her hair, but I could hear her little coos and moans. She was trying to make love to me. Actualized Alex would be cheering right now.

That guy? That ideal Alex? He would be all over Emily Eloise Alessandra St. Claire with a hunger that only true affection can generate. He’d be all over her, touching her body, asking questions to the point of being annoying, making sure he’s giving her the pleasure she deserves, the love and attention and care that she’s shown me, regardless of whether or not she’s been getting paid. Not immediately reaching into her pants because she’s in the driver’s seat—

Yeah, Emily would be in control. So she wouldn’t have to see that what she really wanted was a fucking fraud, that was incapable of not being in complete control of every aspect of his life, who, on top of one cliche of being Captain Save-A-Ho, is now attempting to fuck his massage therapist!

Well, I guess, not ‘attempting’, per se. I’m pretty well in that zone now. But I didn’t do it.

She did.

I was vaguely aware of her sliding off me, still kissing my body, down, down, down. Holy shit. This gorgeous woman is about to suck my dick by intuitively reading my emotional state and not playing with me, but simply interacting. Beautiful.

And the only thing that’s flying through my mind is being deathly afraid of what this COULD mean. And how much I’ve fucking fucked things—

And every single thought disappeared the moment I felt her mouth take my entire shaft down her throat.

My eyes closed and I took a huge breath in through my nose, before getting back to realizing that I’m having sex with a brand new partner. “Hey!” I shout, maybe a little too eager, “did I need to grab a condom?”

A couple more exquisite head bobs on my cock, and a little popping noise as she pulled it out. “Della told me you’re very courteous and fastidious about testing.” Emily giggled. “She said your most recent was two weeks ago, right?”

I rolled my eyes. Blabby, hot little jagoff. “That’s right.”

“Cool. So…”

I rolled my eyes, again. But in a good way.

Her mouth was magic. So warm, so hot, that tongue wrapping around, darting to the head, across my hole. I wanted to hold her there, buck my hips, face fuck her like everyone else. It would be easy, a few thrusts, bust in the back of her throat, out and back home in time for a quick bite and another session—

But I was laying on a girl’s bed, who pulled me into her room, and was working me over like she was getting paid for it.

No.

This was the kind of cocksucking people gave away…to special people.

So I wanted to make it last.

"Hey, let’s get comfy," I said, climbing back up on the bed, and she followed me up, unfortunately detaching from me to straddle my midsection, my hard and sloppy dick leaving stains on her panties.

"Better?" She asked. Then her fingers danced around her panty line, hooking her thumbs in her waistband. "Should I?"

"If you’re, um, okay with that?" Great tone. The questioning would make her feel so safe and not weird.

"Wouldn’t ask if I wasn’t," Emily said, sliding them off and tossing them on my chest. I bunched them under my nose—sweat, spit, powdery clean soap, and an unplaceably sweet and heavy smell.

And there it was, my god. Long, thick, a little pink. It looked so soft. Reaching out, I stopped myself. "Shit, I’m sorry," I said. "Are you okay with me—"

"Yes, dammit, you don’t have to be—but thank you." She took my hand in hers, and guided it over. I grasped it. Yes, it was soft. My hand squeezed, first lightly, then more firm, watching her expression flash with that exquisite pain of someone taking you apart with a touch. It was so fucking gorgeous, the gasp, her chest rising. “Thank you,” she breathed, arching her back, thrusting her chest up and out, letting out a huge breath from her diaphragm.

She bent over and kissed me again, grinding, naked. Naked. In the bed of the most beautiful woman I’d ever seen, choosing me, taking me, without condition.

I rolled over, getting on top, seeing that massive head of hair spread out on her white sheets. Those eyes, looking up at me, anticipation and affection and pure fucking LUST. She licked her lips and spread her legs, letting me sink between them, and I kissed her sloppily in the crook of her neck, nibbling while I suckled the skin. She gasped and moaned, giggled, put her arms around me, her hands, so fucking strong, so stable. Shit. That same feeling with Betty, how I could feel her tiny hands grip not in submission, but connection.

Hands. They did so much. Emily’s long, slender fingers pressed firmly into my back—not the tips, the pads, pulling me in, closer. Beautiful, again, that word just wouldn’t leave my head, more beautiful—

Really? More than Betty?

My mouth moved from her neck to her chest, then her tits, and I put her nipple in my mouth, felt the pert hardness of the skin against my teeth, and sucked. That got a jittery giggle, followed by a breathy moan.

That annoying thought was still in my head. Make a decision, you ass, she’s trying to make love to you.

Okay, Okay! Maybe not, but close. Closer than I expected, and fuck me it was amazing. I was willing to be convinced.

Yes. Because Emily was here. And I was here, with her.

My body was sitting firmly on top of hers now, her legs wrapped around my back, her hold on me more sure than anyone in my life, and she was looking into my eyes…and smiling. That same sweet smile that she had when I ate too many of her free pastries the day we met. When she let me meet her first batch of massage school graduates. Pride and happiness and—

Joy.

Everything she did just made me want her—need her—more. I pressed my hardness against hers, delighting in the slickness on our cocks; then shifted my hips down, let it sit firmly on her sack, and playfully thrusted the flat of my shaft on her taint. She laughed, and its beauty only made me want to work faster, harder, deeper…plant something in that delicate little hole—

Actually, wait.

Still thrusting and grinding, I asked, trying to be as sexy and as slick as possible, “Hey, do I need to grab some lube?”

She shook her head.

Got it.

So I kept going, feeling like I could bust from the excitement alone, us, there, panting and petting and letting our bodies explore.

Emily disengaged for a second. “Did you want to cum now?” She asked, lying under me, legs spread.

“Uh, well, that’s kind of the point?” I leaned down to kiss her again.

She scoffed with my tongue in her throat. “Yeah, I used to think like that too,” she said. “Now lay down.” I rolled onto my back, and she straddled my chest. “Actually, lean up a bit, sit against the headboard.”

Oh, yes. Beautiful.

Quickly in position, she stood, braced herself on the top of the headboard, and lightly thrusted her hips. “Wanna open up?” She asked.

“Kinda question is that?”

“Are you sure?”

“Please. You were nice enough to deep throat me—nothing wrong with returning the favor.”

“I mean it’s—wait. Oh. Alright.” And she thrust her hips again, eagerly, into my willing and ready mouth.

Tasting that soft skin was so much better than just touching it. Her shaft was rock hard. I opened up just a little wide, to give her space to get in, and just leaned back to let her do the work. I heard her make little noises of surrender, softly cooed swear words, tiny gasps she tried to hide, but I knew better—I knew an edging little mess when I saw one. And felt it, twitching and throbbing in my mouth.

“You’ve earned a…bonus…free enhancement," she managed to say. Hard to joke when you’re getting exquisite head—I would know. “My options…are limited…but…” but she was lost in her body, fully given over to pleasure.

However, if she was brave enough to do a bit while getting sucked off, I’d hear her out.

Slipping that perfect cock out of my mouth, I started stroking her a little—low intensity to bring her back, but enough to keep her in the moment. “What was that?” I asked. “Do you have a rewards program?”

She looked down, smiled, bit her lip. “Yes! The first reward is a deluxe scalp massage.”

“And what’s that?” I asked a bit more playfully, firming up my grip.

“Do I need to explain?” And she slipped from my hand, back into my mouth.

Now her hands were in my hair, fingers grazing and pushing and pumping in circles on my scalp, making my entire body tingle as she worked to the back of my throat. As she smacked my uvula around like a speed bag, an undeniably different taste entered my mouth—sugary, sticky, a touch bleachy. The smell of it recalled my teen years, huddled in my room with a sock—

Cum. Pouring down my throat, filling the space under my tongue, thin strands falling with saliva from the sides of my mouth.

“Taste good?” She asked. “I’ll let you have a little more.” She gave me a few more thrusts, and then, as she tried to pull out, I grabbed her ass and tried to push it back in. I was successful, successful enough to catch her off-guard. She lost her footing, moaning and shuddering as she braced herself against the wall. “So needy, Alex,” she said, failing to sound calm and collected. “You’ll get more if you come over again.” Her hand cupped my chin, holding my head in place, and she slowly moved back. Just like that, she was out, and I was devastated.

I reached out again, but her hands caught my wrists. She squeezed them lightly—for her, because Emily’s grip strength was insane. “Aww, no, please,” I whined, making little baby grabby hands.

She let go and got back down, straddling me again. “Poor baby, my sweet cocksucking little baby. Do you still want to cum?”

I nodded. “Yes, please.”

Emily flashed a devilish grin. “Let’s try this.” She rocked back a little, and grabbed both of our cocks, pressing them together. “I’ll try to angle it so you cum on me, okay?”

Her words were fucking static in my head because what I was seeing was too fucking hot. Her hand stroked us together with a fucking metronomic rhythm, a slow, steady pulse, up and down, up and down. The pressure would increase and decrease, like she was reading my body, knowing how to control the peaks and valleys. And the visual of seeing our dicks smushed into her hand, their near equal size—fucking god, it was gorgeous.

She was gorgeous. She started to breathe a little faster, starting to lose a little control, and I could feel her cock start to tense, the head bulging a little bit, the hole glistening with her cum. “Uh…um…that’s not what I was expecting,” Emily said, her abs flexing hard enough to see each individual part of her six-pack. “Kinda…not…used to this…”

Breathing through it like a fucking champ, I took her hand in mine and helped her keep her grip and the rhythm. “You’re doing great, Emily, god, that feels…so…fucking…good,” I moan, feeling my own pressure starting to build, right at the base of my shaft, and moving upwards, inevitably towards the explosion.

Right before it went off, I moved her hand out of the way. "Let me…please," I gasped.

"No…fair, I did all…the work." But she let me take the lead, leaning in and resting her hands on my shoulders. Her head hung over mine, her hair blocking the light, just our faces, so close.

She was so hard, a thin stream was falling onto me already. I wanted her. All of her. I needed her, needed her like sugar in my coffee, beat up paperback copies of my favorite novels, a perfect over easy egg, pristine restorations of my favorite films, or crystal clear remasters of albums I loved as a teenager.

Something that feels frivolous, that looks silly on the outside, but is deathly fucking necessary to feel human. Something that brings joy that we can’t quite explain, that makes our spirits glow when we get it, because it can feel so ordinary but so fucking profound.

That sounded a lot like—

Love.

I didn’t need to take control. I wanted her to have a chance to let go.

She was practically humping my hand at that point, thrusting frantically, desperate for release. “Haah…haah…fuck fuck fuck FUCK god ALEX please just—“ and she lets out a roar, a thick load landing square on my chest. Her thighs quaked, she lost her balance, fell into me, pinning me against the headboard, her form the only thing in the world.

That was it for me, and my seed started with a thick drip, before the spasms hit her in the chest, too.

I finally did the head grab I wanted to try when we first met all those months ago, and kissed her deeply as we both exploded, grunting and gasping and grinding our hips and hands together, squeezing out everything we could, trying to draw it out like it was the end of the world.

And the world didn’t go white. I was right there. With Emily. Just feeling it. Letting go. Letting her in.

We softened, lost the raging white-hot nova, but in its place was a rolling, roiling simmer, a heat easily rekindled at the right moments.

Moments that might…happen more often.

The kiss ended, eventually, but we stayed there, locked together in our embrace. She licked up every bit of her left on my face, and I stole one more kiss, to have one last taste.

No.

Just to hold me over.

***

I woke up.

11pm. Emily’s house.

Tangled up in Emily.

I shook her awake. She grunted, made a hellish coughing noise. "Need a tissue? I don’t think you swallowed anything."

"Shhhh," she said, sleepy and cute. "It’s late and we made love. Bed time now."

We did. "I wish I could stay, but I am not a vital twenty…how old are you again?"

"26."

Excellent, too old to be weird. "—vital 26 year old," I continued, beginning the excruciating process of disentangling myself from her, "and I’ve got medications that must be taken on precise schedules—"

She pulled away, a little smile on her face. "Look who you’re saying that to."

"Oh. Right. Sorry."

"It’s okay, Alex," she said, trailing her fingers across my collar bone, "you have to get home. I’ll be here."

"I know." I leaned over to kiss her cheek. "I’ll be back as soon as I can."

"I know."

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