What the Trans Woman Did to Me in That Hotel

After that first encounter I couldn't think about anything else. I had hired Mariela a couple of months earlier, and although she'd come accompanied by another man then and nothing explicit had ever happened between us, something about it kept going around in my head for weeks. What I remembered most was the way her fingers had explored my ass, that stimulation I'd never allowed myself and that had completely thrown me off balance. Every time I jerked off in the shower, I returned to that image: her pushing a finger into me up to the knuckle while the other guy sucked me off, and me coming like never before all over both their tits.

I filled the emptiness of those weeks with curiosity and a little shame. Every time I closed my eyes, the same image came back, so one afternoon, almost without thinking, I wrote to her. I told her I wanted to do it again, but this time with just the two of us. And I asked her to bring everything she had: toys, ropes, dildos, whatever. I confessed that I'd liked her fingering my ass far too much and that I wanted to go much further, that I wanted her to really open me up.

—Are you sure how far you want to go? —she asked me by message—. Because if you give me free rein, I'm going to wreck your ass.

—I have no idea —I answered honestly—. I want you to decide. Do whatever you want with me.

There was a long pause before she replied with a hotel address and a time.

***

The room was one of those places without any personality: heavy curtains, a bed that was far too big, the constant hum of the air conditioner. I arrived early and waited sitting on the edge of the mattress, my hands sweaty and my cock already half-hard against my trousers, like a teenager. When Mariela knocked on the door, my heart was already racing.

She came in with a small purse and a black cloth bag, which she set on the bed without saying much. She was even more imposing than I remembered: tall, sure of every movement, with huge tits visible beneath her dress and a smile that seemed to know in advance everything that was going to happen.

—I'm going to take a shower —she said, and disappeared into the bathroom.

I kept staring at the bag. Curiosity tugged at me, but I didn't dare open it. When she came out, wrapped in nothing but a towel that revealed the tops of her breasts and her thick thighs, she came over and held my gaze.

—What exactly do you want today? —she asked.

—I want you to use my body like no one ever has —I said, my voice coming out shakier than I'd expected—. I want you to open my ass, to do whatever you feel like.

She smiled crookedly, as if that sentence gave her permission for anything. She asked for payment up front, and I handed it over without arguing. Then, with a calmness that made me more nervous than any haste could have, she told me to get undressed.

I did. She let the towel fall at the same time, and for a moment I didn't know where to look, caught between shyness and a desire I could no longer hide. She had enormous tits with dark, erect nipples, a pussy shaved at the sides with a neat strip of hair left in the middle, and wide hips that gave her an impossible-to-ignore air. My cock hardened instantly, pointing straight at her.

—I see you're ready —she said, looking at my dick with a little smile—. Well, let's take care of that.

***

—Lie down —she ordered, giving the mattress a gentle slap.

I obeyed. From the bag she took two thick cotton ropes, soft to the touch. She tied my wrists to the bars of the headboard, one on each side, carefully testing the knots to make sure they wouldn't hurt me but wouldn't come loose either. Then she placed a pillow beneath my lower back, made me raise my legs and, with another rope, fastened each ankle to the wrist on the same side.

I was completely exposed. On my back, legs spread and raised, my ass lifted and offered up, my cock hard against my belly and my balls hanging in plain sight. I had no room to move except to bend my knees slightly. Pulling on the ropes did nothing, and the feeling of being unable to do anything ran down my back like an electric current.

—Look at you —she murmured, walking around the bed—. Your little ass opened wide for me. What a slut you are, so willing.

She began speaking softly in my ear, telling me things that made my face burn. She described in detail everything she planned to put up my ass, how she was going to stretch me until I begged her to stop, how she was going to use my mouth as if it were another pussy, and promised me, with playful cruelty, that when she was finished she'd leave me like that, tied up with my asshole wide open, so the cleaning staff would find me. I didn't know whether she meant it, and precisely that doubt turned me on even more. My dick throbbed against my belly, already leaking a clear drop from the tip.

She noticed immediately.

—Not like that —she said, shaking her head—. We're not starting with you hard. You're not going to come whenever you feel like it today.

I had to think about anything else, stare at the ceiling, count the cracks in the plaster, until little by little my body calmed down and my cock softened, lying limp against my thighs. Only then did she take a piece of rigid plastic from the bag, a sort of cage with a small padlock. I recognized it from the internet, although I'd never used one. With a gentleness that contrasted with everything else, she fitted it over me, enclosing my flaccid cock inside the transparent plastic, and closed the lock with a sharp click.

Now there's no turning back, I thought, feeling the cold weight of the metal and the total loss of control over my own dick.

***

The game began slowly. She climbed onto the bed and kissed me, first on the mouth, her tongue going deep and playing with mine, then on the neck, biting lightly and leaving reddish marks she knew would last for days. She moved down over my chest, caught one of my nipples between her teeth and pulled until I arched against the ropes. Then she settled over me upside down, in a reversed sixty-nine, so that her pussy was inches from my face while her mouth brushed the cage imprisoning my cock.

I could smell her from there, that warm, wet scent, and see the lips of her pussy parting slightly beneath the weight of the position, already glistening with arousal. I wanted to stick out my tongue and reach her, but she shifted away just a little, leaving her in sight but out of reach.

—Don't even think about it —she murmured—. I'll use that mouth whenever I want.

She ran her tongue over the cage's plastic, knowing I could barely feel anything, knowing that was exactly the point. My cock tried to grow inside its shell but couldn't, pressing painfully against the rigid walls. At the same time, one of her fingers, wet with her own saliva, began drawing slow circles around my asshole without pressing, merely teasing it. Frustration and pleasure mingled in a way I'd never experienced before.

She changed position. She knelt between my spread legs and lowered her head. Her tongue replaced her finger, wet and hot, and I let out a moan I couldn't hold back. I felt the pointed tip of her tongue circling my hole, wetting it all over, then pushing against the center, slipping in slightly, pulling out, and going back in. I pulled at the ropes on pure instinct. No one had ever eaten my ass before, and the sensation was a thousand times more intense than I'd imagined during my mental wanks. She took her time, alternating her tongue with the gentle pressure of her fingertip, covering me in saliva, until I felt the finger slowly beginning to enter me, sliding in past the first knuckle, then the second, sinking in completely.

—Relax —she told me, moving it in circles inside—. You're doing well, faggot. Open that little ass wide for me.

Her finger went deeper, searching inside until it found something, a spot that made me jerk and see stars. She began massaging it with her fingertip, and my cock, trapped in the cage, started leaking precum on its own, a clear thread dripping through the plastic bars without me being able to do anything. Her mouth rose to my testicles, catching them in a suction that was pleasurable and painful at once, sucking first one and then both together inside her hot mouth. I cried several times for her to stop, not because I truly wanted her to, but because the intensity overwhelmed me. She laughed softly against my skin, and the vibration of that laugh against my balls made my whole body shudder.

—We're only just starting, my love. You still have a lot to endure.

She inserted a second finger. I felt the stretch, that sweet burning, and forced myself to breathe deeply. Her two fingers began moving inside me in a scissoring motion, opening me up, and I couldn't stop moaning like a bitch, pulling her ass toward the face of the man looking at me from his tied position. My asshole, which until that afternoon had been virgin territory, was giving itself over completely.

***

From the bag she took a silicone plug, medium-sized, nothing excessive but with a wide base and a rounded body that looked enormous to me from where I lay. She patiently covered it with lubricant, pouring gel over it until it was shiny and dripping, then pressed it against me. The tip slipped in easily, slick, and then came the thick part: there was a moment of resistance, a stab of pain that made me clench my teeth, and suddenly a wet plop as the ring of my ass closed behind the base. A strange fullness made me hold my breath. It was inside me, all the way in, filling me in a way I didn't know how to name.

—Get used to it —she said, and then did something I hadn't expected: she stood up, sat in the chair beside the window, still naked, with her legs crossed in a way that let me see a strip of her pussy, and took out her phone.

I called to her softly, but she put a finger to her lips, asking me to be quiet while she talked to someone about trivial things, as if I weren't there, tied up with my caged cock leaking and a plug thrust through my ass. The waiting was its own torture. Every minute stretched on while my body adjusted to the plug, while my asshole grew accustomed to being open, and my mind wandered between humiliation and the desire for more. Every time I moved even slightly, the plug shifted inside me and brushed my prostate, sending jolts through me that made me moan softly, clenching my teeth so I wouldn't interrupt her call.

When she hung up, she came over again and grabbed the plug's base, moving it slowly, pulling it halfway out and pushing it back in, fucking me with it for a while until I was writhing against the ropes. Then she withdrew it in one slow movement, pulling it out completely, and I felt my ass left open for a few seconds before closing again, this time not as tightly as before.

—Almost —she murmured, more to herself than to me—. But it still needs work. You still have to open up more for me.

I didn't understand what she meant until I saw her take out another object. It was an inflatable dilator, with a rubber bulb like the kind used to measure blood pressure. She lubricated it thoroughly and inserted it carefully. At first it went in deflated, almost without resistance after what had come before, and she began pumping.

In the wardrobe mirror I could see it widening inside me with every squeeze of the bulb. I felt my inner walls give way, felt the ring of my ass stretch centimeter by centimeter. It didn't hurt, at least not as much as I'd feared, but the pressure kept growing until it became the absolute center of all my sensations. One more pump, then another, and another. I could no longer think of anything except that impossible dilation. I decided to let my body go, breathe deeply and surrender. She continued until it was fully inflated, a huge balloon inside me, leaving me that way, open and throbbing, my asshole stretched obscenely around the dilator's neck.

***

While I tried to process all that, she positioned herself in front of my face, kneeling on my chest, her wet pussy millimeters from my mouth. At last. She lowered herself onto my face without asking, sitting on my mouth with all her weight.

—Lick —she ordered—. Lick my pussy like it's the last thing you'll ever do.

And I obeyed. I stuck out my tongue and licked her lips, moving up and down along the slit, finding her swollen clit and sucking it eagerly. She began moving on top of me, riding my face, rubbing her pussy against my mouth and nose. What came next literally took my breath away: she used my face at a brutal pace, grinding it against her pussy, barely letting me breathe between thrusts. Her taste filled my mouth, salty and sour, and I felt her juices running down my chin and neck. I felt nauseous when she pressed my nose into her pubis, my eyes filling with tears, but there was also a dark pleasure in me I hadn't known existed. I endured it, wanting to last, wanting to prove I could serve her. I pushed my tongue as deep as I could into her pussy, fucking it with my tongue, and she moaned for the first time in earnest, a guttural growl that made me understand she was enjoying it too.

She came on my face. I felt her thighs squeeze my head, a tremor running through her whole body, and a warm gush of wetness bathing my mouth and chin. She made me swallow everything, pressing me hard against her until the spasms ended.

She moved away just in time, panting, her hair stuck to her sweaty forehead. She lowered herself between my legs again. She deflated and removed the dilator with a firm movement, and the sudden emptiness made me moan. My ass must have been open like a flower. Then she put on a long latex glove that reached to her elbow.

—This is what you need —she said, coating her hand in oil until the glove was shining all over.

She pushed. She brought all five fingers together to form a cone and pressed them against my asshole. She tried several times, looking for a way to get her whole hand in. I felt her knuckles pushing against the ring, felt my ass stretching in a way that was no longer pleasurable but savage. A cramp ran through my legs and I screamed for real, a hoarse cry from deep in my chest. She couldn't do it; my body couldn't take that much, and instead of forcing it, she changed tactics. She began moving three or four fingers in and out at a steady rhythm, fucking my ass with her hand, each thrust deeper than the last. With her other hand she stroked me through the cage, squeezing my swollen balls hanging beneath the plastic, tugging at them lightly.

It was perfectly calculated cruelty: she stimulated me without allowing me anything, keeping my body on the edge without letting me cross it. Her fingers kept moving inside me, finding my prostate again and again, massaging it with the middle finger's tip while the others opened my inner walls. I writhed against the ropes, pushing my ass against her hand, begging for more, deeper, faster, like a bitch in heat. Until, against all logic, I felt I was about to finish.

—Come —she whispered—. Come for me without touching your dick, like a bitch. Come with my hand in your ass.

The orgasm came trapped, in drips, without the erection the cage prevented. It was a strange release, a long spasm that shook my hips while semen came out in a weak, awkward stream through the caged tip, dripping through the plastic bars and falling onto my balls and belly. Intense and frustrated at the same time, accompanied by a dull ache in my testicles that made me clench my teeth. She didn't stop moving her fingers inside me throughout the orgasm, milking me, wringing me out to the last drop. I was left panting and trembling, tears in my eyes, unsure whether what I'd just felt was pleasure or punishment. A little puddle of white fluid collected on my stomach, mixed with lubricant and sweat.

***

Mariela slowly pulled out her fingers, and I felt my dilated ass taking a while to close, remaining slightly open, throbbing, for a while. She stood up unhurriedly. She removed the glove, went to the bathroom and showered while I remained tied up, catching my breath, the semen cooling on my skin. When she came out, she removed the cage, finally freeing my cock, which was sore and red, and began gathering her things, putting each toy back into the black bag with the same calmness with which she'd taken them out.

—I'll give you the ropes —she said, amused—. And if you want to do this again, you know how to find me. Next time I'll put my whole fist in you, I promise.

—Wait —I said, still with my wrists tied—. Untie me.

She only smiled. She picked up her purse, slung the bag over her shoulder and walked toward the door.

—Mariela, seriously —I insisted, now with a knot of fear in my stomach—. Don't leave me like this.

—Someone will come —she said from the doorway, without turning all the way around—. Trust me.

And she left.

***

The silence of the room became enormous. I pulled at the ropes, but the knots held. Tied on my back, my ass still dilated and half-dried semen stuck to my skin, unable to call for help, all I could do was wait and pray she hadn't lied about someone coming.

About fifteen minutes later I heard banging on the door. I shouted for them to come in, that the door was unlocked. I assumed Mariela had alerted the hotel staff before leaving, as one last move in her script.

Two maintenance workers came in. When they saw me in that situation—naked, tied up, legs spread, still gleaming with oil and semen between my thighs—they froze for a second and then laughed under their breath, covering their mouths. My face burned with embarrassment, but I decided to take it with humor and joked with them while they came over to untie me.

—It's not the strangest thing we see in this job —one of them said, undoing the knots without looking too far down.

When my hands were finally free, I thanked them and apologized a thousand times. I took some money from my wallet to compensate them for the awkward situation and for their discretion. They took it naturally, wished me better luck next time and left amid restrained laughter.

***

I sat on the edge of the bed, sore but strangely satisfied. My whole body was asking for rest, and every muscle reminded me of what I'd just experienced. My ass throbbed, open and burning, and when I ran a finger over it to check the damage, it felt loose, different, as if it would never be the same again. I stayed like that for a while, staring at the empty bag that was no longer there, the ropes still hanging from the headboard, the absurd gift she'd left me.

I dressed slowly, still red with embarrassment, but wearing a stupid smile I couldn't erase. I'd arrived at that hotel without knowing what I was looking for, and I was leaving with the certainty that I'd crossed a line I had no intention of uncrossing.

I put the ropes in my coat pocket. Just in case. Something told me it wouldn't be the last time I called her.