My Roommate Discovered My More Feminine Side

I look like any other man, though I know I don’t quite fit that mold. I like women, that’s true, but there’s a part of me that only settles when I imagine myself in a man’s arms, caressed, held, desired, with a hard cock thrusting into me. It’s something I’ve carried with me for years, and almost no one knows about it.

I have a slender, hairless body, naturally smooth. I shave away the little that grows and soften my skin with cream every night. I like the way I look this way: smooth, sleek, almost feminine under the bathroom’s warm light. I run my fingers over my round ass, touch my tight little hole, and imagine a thick cock forcing its way in, opening me slowly.

In the privacy of my apartment I transform. I put on women’s underwear, sheer stockings, a black garter belt I bought online with my heart pounding. I look at myself in the full-length mirror and recognize myself in that image better than in any other. That’s how I truly feel. Sometimes I slip a finger slicked with saliva into myself while I watch, and I come all over the floor thinking of a man fucking me without mercy.

I had never shown that side to anyone. I kept that secret under lock and key, among shut drawers and lonely nights. Until that conference came along.

***

The company held a several-day gathering for all the staff every year, and that time they did it at a resort by the sea, on the coast. They assigned us double rooms, two people per room, and I was paired with someone who had recently joined the company.

His name was Damián. A mature man, around his forties, tall, with neatly kept gray hair and an easy smile. Kind, talkative, with that calm self-assurance years bring. We barely said hello when we arrived, unpacked our bags, and each of us left for our own activities. We exchanged no more than four sentences.

The first night I got back to the room early, exhausted. I took a long shower, put on a small pair of sleep shorts, and climbed into bed. I was half asleep when I heard him come in, carefully, making no noise. I didn’t open my eyes.

The second day was the closing event. There was a toast that turned into a party, because the mood was cheerful and the alcohol flowed freely. I drank more than I should have and at some point felt my head spinning, so I decided to leave.

I went back to the room, showered again to clear my head, put on my usual shorts, and lay down in bed. Damián was still downstairs. Before I left, I’d seen him laughing with a group, dancing with a couple of female colleagues, flirting with one or another. I thought maybe he wouldn’t even come back to sleep that night.

I fell asleep without noticing.

***

I don’t know how much time passed. The sound of the door opening woke me. In the dim light I saw Damián come in unsteadily, a glass of liquor in his hand. He walked toward his bed and, with spectacular bad luck, tripped and spilled almost all of it onto the sheets. He muttered a curse under his breath and started feeling the mattress.

—Shit —he murmured—. It’s soaked.

I watched it all with half-closed eyes, pretending to sleep. After a moment he came over to my bed and spoke softly.

—Hey, buddy —he said gently—. Could you make some room for me? My bed got wet and there’s no way I’m sleeping there.

I could have told him no. I could have suggested he call reception to change the sheets, or ask for another room. It was three in the morning, but something could have been done.

I did none of that.

Instead I shifted to one side and gave him room. These were big beds, the large kind; there was plenty of space for both of us. Why did I do it? Was it really just courtesy?

During the party I had looked at him more closely. Mature, yes, but with a firm, elegant body, clean-shaven, impeccably dressed. That morning, when he left the room, he had left behind the scent of an expensive cologne. I found him attractive, and I told myself it would be rude to leave him adrift at that hour. That’s what I told myself.

—Thanks —he whispered, and started taking off his clothes.

Being respectful, I turned my back and arranged my pillow as if I were going to keep sleeping. I felt the weight of his body sink the mattress, the rustle of the sheets, and then his scent reached me mixed with the sweet breath of alcohol.

He started talking to me in a murmur. He had a deep, masculine voice, one of those that slowly gets under your skin. He commented on the meeting, the people he’d met, the night’s anecdotes. I replied in monosyllables, pretending sleep was overpowering me. The truth was different: I was aroused, my cock swelling inside my shorts, my whole body on alert at having a man that close.

After praising one female colleague after another, he asked directly:

—And you? Which girl do you like?

I stayed silent. Silence filled the whole room.

***

Then what I feared most happened. Or what I most wanted; I wasn’t sure anymore what the difference was.

Damián moved closer. His voice dropped until it was barely a thread by my nape.

—You know? I’ve been watching you —he said—. Last night, when I got in, you were asleep. It was hot and you’d kicked the sheets off. I couldn’t stop looking at you. With those tiny shorts on, your legs looked gorgeous. And that little perky ass of yours, fuck, I got hard right then just looking at it.

—Please don’t go on —I begged in a thin voice—. You’re drunk.

He came even closer. I still had my face to the wall, not daring to turn around.

—Don’t take it the wrong way —he continued—. I have a gift for knowing when someone likes me, whether woman or man. And I know you’d like me to hold you, kiss you, eat your mouth and more. —He paused—. Besides, I like you too. I get hard just having you next to me.

With every word he closed the distance. I, trembling, inched toward the edge of the bed, with no courage to stop him or face him.

—Come on —he insisted—. Let yourself be loved. I know you want it. I know you want me to fuck you.

Suddenly he wrapped an arm around me from behind and pulled me against his body. That was when I understood: he was completely naked. I felt his skin against mine, the coarse hair on his chest against my back, and the hard, hot, heavy bulge of his cock pressing between my ass cheeks over my shorts. I froze, stunned, eyes wide, and a small gasp of fright escaped me.

He pressed his mouth to my ear and started speaking softly. I didn’t even register the words. The sensation was pleasurable and terrifying at once. One hand held my waist while he pressed his legs against mine and rubbed his cock slowly against the fabric of my shorts, tracing the crease of my ass with his hard dick.

I felt like I was dying of shame, modesty, anxiety, and desire, all tangled together. I wanted to get up and run, but my body didn’t respond, as if one part of me had decided for the other and was keeping me still on purpose.

***

He brought his pelvis to my backside and pushed harder, grinding that thick cock between my ass cheeks. Another moan escaped me, this time involuntary, and that seemed to turn him on even more. He began kissing my neck, licking behind my ear, gently biting my earlobe, running his open palm down my legs, up the thigh until it brushed the hem of my shorts.

He slipped his hand inside and took hold of my cock, already hard as a rock. He let out a low, satisfied laugh at the discovery.

—Well, look at that —he whispered—. You’re rock hard. Stop lying to me, baby. Your cock speaks for you.

He started jerking me off slowly, his hand closed in a warm fist that moved up and down with a lazy rhythm. His thumb stopped at the tip, rubbed it in circles, and I bit my lip to keep from crying out. His other hand pinched my nipples, tugged at them, squeezed them, while his mouth never left my neck. I felt a drop of wetness run down his hand, my own fluid leaking out, and he used it to slide his fist more easily up and down my cock.

—That’s it, come whenever you want —he murmured—. We’ve still got the whole night.

He stayed like that for a good while and I let him do it, with no strength left to resist, surrendered to that voice and that hand. He pulled my shorts down and, when they reached my knees, I was the one who kicked to finish taking them off.

—That’s it —he murmured, pleased—. Show me that little ass.

He flipped me onto my back in one tug and buried himself over my mouth. His tongue entered without asking permission, thick, hot, seeking mine. I opened my lips and let him, sucking him with the hunger of years. He kissed me while his hand kept squeezing my cock, and I felt his, hard and thick, pressing against my hip.

He went down my neck, my chest, pausing at each nipple to suck until they hardened and he drew a sharper moan from me. He kept going down my stomach, and when he reached my cock he took it at the base and swallowed it all in one go.

—Ah, fuck! —I blurted out.

He sucked me like he’d wanted it his whole life, his mouth to the hilt, tongue wrapping around me, lips tight as they moved up and down the shaft. He pulled my cock out of his mouth to lick my balls one by one, then took me in again. With one hand he held my thighs apart and with the other he stroked my ass, pressing his middle finger against my entrance.

—You taste so good —he said with his mouth full—. And you’re so tight back here.

He lifted my legs and folded them against my chest, leaving me fully exposed. He lowered his head and I felt his hot tongue on my hole. I nearly died. No one had ever done anything like that to me. The tip of his tongue traced circles, pushed in, sank, came out. He was eating my ass with the same hunger he’d sucked my cock with, and I writhed in the sheets, moaning loudly, no longer remembering shame.

—Please —I begged him without knowing what I was asking for—, please…

He sat up halfway, placed a cushion behind him, and leaned back against the headboard. For the first time I saw his cock in full: thick, long, with the glans swollen and shining with our saliva. He guided me to straddle him, my legs on either side of his body, and drew me toward him as if I were fragile. With both hands he took my ass again, kneaded it, squeezed it, parted it.

—Suck me first —he asked—. I want to see you with my cock in your mouth.

I slid down his body and took him in my hand. It was heavy, throbbing. I gave the length a long lick from his balls to the tip, and he let out a guttural groan that made me hotter. I opened my mouth and took him in, first just the head, tasting the salty flavor of the fluid leaking from him, and then I went lower, as much as I could, until the tip struck the back of my throat and gagged me.

—That’s it, easy, no rush —he guided me with a hand on the nape of my neck—. Suck me nice and slow.

I sucked him like in my fantasies, bobbing my head up and down, listening to his gasps, feeling his thighs tense under my hands. I licked his balls, ran my tongue under the glans, sucked his frenulum, and he stroked my hair, murmuring that I was a pretty little faggot, that I sucked cock like a goddess.

—Come here —he said at last, pulling me up—. Now then, sit on my cock.

I mounted him again, and one of his hands reached lower, between my legs, and began probing my entrance. I jerked, but he held me tighter to calm me. He grabbed a jar of cream that, conveniently, had appeared on the nightstand, and coated his fingers with it. He started massaging my hole with the cold, slippery gel until the tip of one finger slid in.

—Relax, baby, let me get you ready.

I felt the finger forcing its way in little by little, all the way to the base. Then a second. Then a third. He moved his hand in circles, pulled it out, pushed it back in, stretched me patiently while the other hand slowly jerked me off to distract me. When he found something inside me that made me jump and cry out sharply, he smiled.

—There it is —he murmured—. There’s the button.

He began rubbing that spot with his fingertip, and I was coming apart over him, riding his fingers, asking for more without words.

When he felt I was ready, he coated himself too, smearing cream all over his cock until it shone, and guided me little by little. He aimed the glans at my entrance and, with slow, firm pressure, pushed in. I felt pleasure mixed with a stab of pain that made me breathe deeply. The head made its way in, then the whole shaft, and I lowered myself millimeter by millimeter, biting my lips until I felt my thighs rest over his and his balls touch my ass.

We stayed still for a moment. I was trembling, speared on that thick cock that filled me completely. He stroked my back, kissed my neck, waiting for me to get used to it.

—You’re so tight, my love —he panted—. You’re squeezing my cock.

Then he began a gentle back-and-forth, almost rocking, and the discomfort became imperceptible. I myself began to move, slowly rising and lowering over him, rotating my hips, discovering the new pleasure of having a man buried in me to the hilt. With each descent his cock hit that spot inside me and drew a longer, rougher moan from me.

—That’s it, ride me —he encouraged—. Ride that cock like the rich little slut you are.

***

After a while he made me lie on my side, both of us facing each other, without separating, with one of my legs lifted over his hip. He set a slow rhythm, withdrawing almost all the way before plunging back in, and sighs escaped me that I no longer tried to hold back. With every thrust I felt his cock opening me from within, his balls hitting my ass, his mouth never stopping biting my neck.

—You like it, don’t you? —he whispered between thrusts—. Tell me you like me fucking you.

—Yes —I gasped—, yes, I love it, don’t stop…

—Louder —he demanded, driving in harder—. Say it louder.

—Fuck me! —I moaned—. Fuck me harder!

He laughed softly, satisfied, and turned me onto my stomach. He positioned my hips up, my face buried in the pillow and my ass lifted as an offering, and got down on his knees behind me. He entered again in one thrust, all the way in, and I screamed into the pillow.

Then he really started fucking me. No more gentleness. His hands squeezing my hips, pulling me back with every thrust, skin slapping against skin in an obscene splash that filled the room. I clenched the sheets in my fists, mouth open against the pillow, letting myself be used, letting that man ride me like I’d wanted for years.

Then he settled over me, covering me completely with his body, and kept thrusting from above while whispering obscenities in my ear. The sensation of his weight on top of me, of feeling covered and penetrated at once, drove me insane.

—I’m going to fill your little ass, you hear me? —he panted against my nape—. I’m going to leave all my come inside you.

—Yes, inside, give it all to me inside —I begged.

He slid a hand under my body, grabbed my cock, and started stroking me in time with his thrusts. I couldn’t take it anymore. The combination was too much: his cock hitting that button inside me, his fist crushing me outside, his teeth on my shoulder. I felt the orgasm climbing from my balls, uncontrollable, and I came over the sheets in hot spurts, moaning his name for the first time.

—Damián!

My ass clenched in spasms around his cock, and that finished him. He clung to me tightly, tensed every muscle, and with a long shudder, reached climax inside me. I felt the hot spurts filling me, one after another, while he kept pushing slowly, emptying himself completely into my body. He stayed still for a while, still joined to me, catching his breath over my back, his cock still throbbing inside me. Then he withdrew slowly, with a deep sigh, and I felt the warm thread of his semen dripping down my thigh.

I didn’t even want to move. I was in some kind of trance, exhausted and happy at once. I had surrendered to a man who had seduced, dominated, and possessed me in a single night, and the most disturbing thing was that I had loved every bit of it. Every caress, every word in my ear, every inch of cock, every second of that surrender.

I stayed face down, breathing slowly, still feeling the warmth of his semen inside and outside me. I turned my head and looked at Damián, who was already sound asleep, oblivious to the whirlwind he had unleashed in me.

I curled up beside him. I caressed his chest, his stomach, tenderly while he breathed peacefully. I rested my head on his shoulder and lifted one leg over his, seeking his warmth.

I thought about my locked drawers, about the stockings and garter belt hidden at home, about all those years of secrecy. That night, for the first time, someone had seen the person I really was, and instead of running, he had fucked me until I moaned his name.

I closed my eyes with a smile and let sleep take me, pressed against the body of the man who, without knowing it, had given me permission to be myself.