Confession: What I Did on That Trip with My Coworker
My name is Mateo, and I’m thirty years old. During university I had several encounters with other men, a phase I decided to close the day I met my wife. I’ve been married for six years, we’re parents of two children, and four years ago I moved from Medellín to a coastal city in the Colombian Caribbean to work in technology for a port logistics company. It’s a small, conservative city where everyone knows everyone else. Even though I sometimes missed those university years, I was never going to put my marriage or my reputation at risk for a fleeting horniness.
My coworker’s name is Damián. He’s around thirty-seven, tall, athletic, plays soccer on Saturdays, and works out at the gym four times a week. He’s divorced: his ex-wife couldn’t put up with his cheating. Now he lives common-law with a twenty-one-year-old girl, a beautiful woman, and even so he still sleeps with anyone who crosses his path. Everybody knows it. I’m sure his partner does too.
Besides being handsome and manly, he’s witty and friendly, which is why he has no trouble picking up women. Once I asked him how he could go around with just anyone when he had such a pretty partner at home, and whether he wasn’t afraid of losing her the way he lost the last one. He laughed, put his hand over his crotch, and answered me.
—Truth is, yeah, I’ve thought about it. I don’t know how my girl puts up with me. But this head doesn’t think.
I just smiled at the joke.
A few months ago they chose me to attend an international conference being held in Cartagena. The other person chosen was Damián. The company paid separate per diems for lodging, food, and transportation, but the amount wasn’t enough to stay at the luxury hotel where the event was taking place. I was looking for cheaper alternatives when Damián had an idea.
—What if we ask for a double room and have them bill each of us separately?
The idea seemed brilliant to me. The double room cost the same as a single, so split between us it would be no problem. On top of that we saved on transportation, which was paid in cash and without receipts, and we had the convenience of going up to the room whenever we wanted. I called the hotel, they had no objection to splitting the bill between two people, and I made the reservation right then and there.
We traveled on a Sunday. We arrived at night, checked in, left our bags, and went downstairs for dinner. Everything was normal. It was summer and it was hot, so as soon as we got back up to the room I felt like taking a shower. While I was bathing, Damián came into the bathroom to piss. The shower was separated from the rest by a completely transparent glass panel. I could see him, he could see me. Out of the corner of my eye I saw him pull out his cock. Even at rest it was a long, thick cock, with the foreskin pulled back. The stream was strong. The image started to get to me and I noticed myself growing under the water. So he wouldn’t notice my agitation, I turned toward the wall, leaving my ass on display. I heard him let out a low whistle.
—You’ve got a great ass, Mateo.
I felt caught out. I turned back toward the shower, covering my half-hard cock with my hand. I caught him shaking off the last drops, tucking his bulge away, and smiling. He winked at me and left the bathroom, leaving me frozen, embarrassed.
Once I relaxed, I finished showering. I dried off, put on a pair of boxers and a long T-shirt, almost like a nightshirt, and went out. It was his turn. Without the least embarrassment he stripped completely naked, took a towel, and walked into the bathroom. I couldn’t help looking. He had a broad, athletic back, defined legs, and a small but firm ass, slightly hairy. A macho ass.
When I heard the water running I turned toward the wall and pretended to sleep.
He came out, wished me good night, and turned off the light.
It took me a while to fall asleep. The image of his naked body wouldn’t leave me, and the comment about my ass kept turning over in my head. But being the heterosexual, womanizing macho I was, I took it as a joke.
***
The next day we got ready and went down to the conference. The first day was intense and enjoyable, there was a break with snacks and coffee, and almost without realizing it we were done for the day. After lunch we went back up to rest for a while. Damián wanted to go to a strip club he’d heard about, he said there were foreign models there and some stripped completely. I agreed, out of curiosity and to do something different for a while.
The place was exactly as promised. Beautiful women dancing, some with nothing on, others walking between the tables. After a while two sat down with us and asked us to buy them a drink. The usual thing, I knew it was the strategy to get money out of you, but those two were worth it. We spent a couple of hours drinking, talking, and taking advantage of every chance we got to touch whatever they’d let us touch. When it got late, Damián wanted to take them back to the hotel. He asked the manager the rate and was told an exorbitant figure, well beyond our reach. We left there hot and a little frustrated.
We smelled of alcohol and cigarettes. We needed the bathroom. I gave him the first turn. He stripped, as always, and this time I noticed his cock was semi-erect. A thick, long piece of meat that sent a shiver through me. I felt my hole contract from pure anxiety.
He came out, took off the towel, and put on a pair of boxers. The bulge was so large it looked ready to burst through the fabric. Imposing. Almost obscene.
I got into the shower thinking about that cock. When I finished, I realized I’d forgotten my boxers outside. I didn’t care. Maybe because of the drinks I’d had, I felt uninhibited. If he didn’t mind walking around the room naked, I didn’t see why I couldn’t do the same. I came out with the towel, dried myself on the bed, and walked to my suitcase.
The normal thing would have been to put the suitcase on the bed or bend my knees to open it. But I spread my legs a little and bent down without bending them, showing my ass. I felt the cool air running through the groove of my butt cheeks, caressing the opening. I took a while looking for my underwear, pretending not to find it, a product of the alcohol in my system. At last I chose some stretchy boxers, tight fabric like a glove, and put them on without turning around. My cock was hard. I was aroused and I didn’t quite know why. Maybe because of the drinks. Maybe because of that compliment about my ass, and the absurd desire for him to savor it, even knowing nothing would happen.
I got under the sheets quickly so he wouldn’t notice my erection. I said good night. I caught a glimpse of him settling his cock under his boxers. I turned toward the wall and pretended to be asleep.
Little by little I drifted off. In the middle of the night I woke to a soft, pleasurable sensation. Damián was stroking my ass over the fabric. Just a brush of contact. He was trying not to wake me. I kept my eyes closed, pretending to sleep, and as if in a dream I bent one knee to open myself a little. I couldn’t believe it. My coworker, so macho, so womanizing, was stroking my ass.
The boxers gave way under his hand. He slid his hand under them and started touching the skin directly. My breathing quickened but I didn’t move. Seeing I wasn’t reacting, he pulled the boxers down to the start of my ass cheeks. A finger slid down the groove and brushed my hole. I had to bite my lips not to give myself away. My whole body trembled and he jerked his hand back, thinking I’d woken up.
I stayed still, breathing deeply, pretending to keep sleeping. A few seconds later I felt his finger again, now slippery, with the cream they give you in hotels. He caressed the outer folds of the sphincter in a delicious way. I bit the pillow so I wouldn’t moan. After a few minutes he pressed. The tip went in, came out, went in again. I loved it. I arched my waist to offer him more, and then his finger went all the way in.
He moved it in circles, rubbing the inner walls, lubricating me from within. I kept biting the sheets and smothering my moans.
—Do you like it?
It was impossible to keep pretending. A rough moan escaped me.
—Mm... uh-huh.
Now without caution, he drove the finger deep inside me. I writhed with pleasure. He found the prostate and the moans increased. He moved it from side to side, in and out, as if he were fucking me with a finger. I rolled onto my stomach, lifting my hips. With his free hand he pulled my boxers all the way down until I was naked.
—My God, what a little ass. It squeezes deliciously. You can tell it was hungry. If I’d known you were like this, I would’ve fucked you years ago.
In response I spread my legs wider and arched my ass higher, in a sign of absolute surrender. Another lubricated finger joined the first. The sensation doubled and I jolted. His fingers explored without restraint, scissoring open, and I felt fresh cream filling my ass. When he judged me well stretched and lubricated, he pulled his hand out. I knew what was coming. I arched higher.
He took a pillow and put it under my hips. He lay down over me. His chest against my back, his hot breath on my ear.
—You’re ready now, little slut. Now comes the good part. Get ready to scream with pleasure.
His slab of meat, hard and hot, ran along the groove between my cheeks. Up, down. It rested on my hole, rubbed, slid down to the balls. He was taking me to the limit without having even entered me yet. The folds of my hole tightened and relaxed, longing to feel that thick mushroom rooting around inside.
—Can you feel my cock? Do you notice how thick and hard it is? You’re going to come like a slut when I put it in you.
In my head I was already imagining myself impaled by that enormous cock, screaming with pleasure. I wanted it inside me. I couldn’t take it anymore.
—Put it in, please. Even just the tip.
—Really? You want me to fuck you in the ass? Ask me again, like a good little slut.
—Put it in, Damián. I want to be your little faggot. Please.
—Very good. But you’re not going to be my little faggot. You’re going to be my little slut. I’m going to make you my female. Is that clear?
—Yes, whatever you want. Your female. Your little slut.
The last word turned into a moan when he pushed the head of the burning cock in. It went in millimeter by millimeter, opening my folds. He put in just the tip, pulled it out, pushed it in again. Each time a little deeper. Until, holding me by the waist, the entire glans pushed through my narrow hole and sat buttoned up inside. It hurt. The fibers stretched to the limit. I bit the pillow so I wouldn’t scream.
—The head’s in now, my love. My cock is very thick. But it goes in you just fine. This definitely isn’t the first time your ass has been torn open, am I wrong?
—No. When I was in school I got fucked. But that was a long time ago.
As I said it, flashes of those university lovers came to me. Flashes of my wife also came, of my parents, of my friends. What would they say if they saw me like this, naked and spread-legged, speared by another man like a female?
I could feel the head of his cock throbbing inside me, hot, hard and soft at the same time, keeping the first part of my ass wide open. I felt numb from being stretched so much.
—That’s right, princess. Your little ass remembered how to open. But it squeezes deliciously from lack of use. Don’t worry, I’m going to leave it like a little pussy. Want more cock?
—Yes, more.
He pushed in another three or four centimeters. He began a slow back-and-forth, fucking only the entrance. I needed all of his cock and begged him.
—Put it all in, Damián. I want to be yours. Impale me all the way to the balls.
He smiled.
—Very good, little slut. You’ve earned it for being such a good whore.
He grabbed my waist and pushed, slow but without stopping. I could feel the folds stretching to let him through. Soon I felt the rough hair against my ass cheeks and his balls slapping mine. I was completely speared by that beautiful cock. A sensation of fullness that’s hard to describe, as if I might burst.
The thrusts began. Slow, deep. Hot flesh throbbing inside me, rubbing the inner walls, hitting my prostate with every push. A pleasure that ran through my whole body and made me moan.
—Fuck, what a good ass, baby. You have no idea how much I’m enjoying this. You’ve got a classy little slut’s ass. It swallows the whole cock, all the way to the balls, but nice and tight. You’re going to make me cum and I don’t want to, I want to keep enjoying your little ass.
Suddenly he pulled all the way out and I felt a void inside me. My hole remained stretched, open, not closing. I was about to protest, ask for more, when he said:
—Wait. I was about to blow. But first I want to fuck you face-to-face. Like a female. Turn over.
I rolled onto my back. He opened my legs and settled himself between them. He started stroking my thighs, my hips, my waist, my belly. My skin prickled at the contact. He went up to my nipples and pinched them, drawing a stifled moan from me. He reached my lips and stroked them with his fingers. He put two fingers in my mouth, pulled them out damp, and brushed my lips again.
Then he bent down to kiss me everywhere. The belly, the chest, the nipples, alternating tongue and teeth. I twisted in his arms. I was in heaven. He came up to my neck, kissing and licking it while I felt his chest pressed to mine, his heat, his dominance. He was making me feel like his woman. He reached my ear, slipped his tongue inside, and an electric current shot through my whole body.
—Your skin is so soft, gorgeous. It’s a pleasure to touch you. What I’d been missing. But don’t worry, you’ll be mine from now on.
His mouth sought mine. His tongue slipped in and tangled with mine. A burning kiss, a macho kiss. I hugged him and stroked his muscular back. He whispered in my ear.
—Are you ready to be completely mine? My female.
—Yes, daddy. I want to be yours. I want you inside me. Fuck me.
—I’m going to fuck you like a female and you’re going to stop being a little faggot and become my female. I’m going to fill you up inside. I want every time you have sex with your wife to remember me. How I impaled you.
—And I want every time you fuck yours to remember me. How you made me your female. How tight I had it and how much you enjoyed my ass.
—That’s how it’ll be, queen. I hardly ever fuck my partner in the ass, not many can take it. You’re a champion. You’ve made me enjoy myself like nobody else.
He took my legs, lifted them, and bent them toward my chest. I held them with my hands to keep the position. He put a pillow under my hips. My ass was lifted and open, exposed, at his disposal. He placed the head of his cock at the opening and began opening me again, slowly, until his balls hit my ass cheeks. In this position he went even deeper and the head stretched my ass from the inside. Completely impaled.
He started moving his pelvis. His face was pure lust, pure perversion. His eyes gleamed with malice. He smiled as he fucked me, enjoying having dominated me, having turned me into his girl.
—I like seeing your little slut face when I fuck you. Seeing how much you enjoy my cock. It gets me so turned on. Do you like it, baby?
With every thrust I sighed, moaned, writhed with pleasure. He sped up and slowed down according to my reaction. Sometimes he left it all the way inside me, pushing his pelvis against my ass cheeks, other times he moved it in circles massaging my prostate. I lost track of time. Everything spun around me. It was a sublime pleasure. I started convulsing. My eyes rolled back. I felt myself fading. My cock exploded on its own, untouched, and streams of semen fell between our two bodies.
—That’s it, baby. You came like a female. Ahh, so good.
That excited him even more and he started fucking me furiously. The spasms of my ass squeezed his cock. He kept boring into me without mercy until he could hold back no longer and, with one last deep thrust, unloaded inside. A generous, hot cumshot that flooded my ass with his nectar.
He collapsed onto my body without pulling his cock out and gave me a burning kiss. I hugged him and stroked his head and back. Little by little he lost his hardness and slipped out, along with a thread of semen that ran down my cheeks. At last I could stretch my legs. They were shaking, numb from it all.
He helped me up and we went to the shower. With his semen still dripping down my thighs, he washed me tenderly, like I was a little kid. Afterward we lay down in his bed, because mine had been left in a mess. He held me in his arms. I rested my head against his chest and we fell asleep like that, naked. I truly felt like his female. Now I understood, and experienced firsthand, why he had so much success with women.
***
The next morning I woke up first. I was embarrassed; I didn’t know how he was going to react. I was drying myself after showering when he came into the bathroom, saw me, and hugged me tightly. He gave me a warm kiss. An unmistakable sign that he hadn’t forgotten a thing.
—Fuck, Mateo, what a night. I’ve never enjoyed myself like that. You’ve got the best ass I’ve ever fucked. No woman has ever made me feel like you did. What happened last night has to happen again. I want you to be my woman. Will you accept?
I was left speechless, confused. I was thinking about my family. He saw my face and added:
—Don’t worry. You’ll only be my woman in private. For our partners and everyone else, we’ll keep being friends. It’ll be our secret. Deal?
I didn’t answer. I kissed him. Nothing else was needed.
The following days we didn’t leave the hotel. During the conference everything went on normally, but as soon as the lectures ended we locked ourselves in and fucked like animals. Damián had stamina. He fucked me in every imaginable way. He left me tired, exhausted, with my ass burning, but happy. I never imagined my return to being with a man would be so formidable.
When we returned to our city, we went on with normal life. But something had changed. In front of everyone —our partners, friends, coworkers, acquaintances— we were the best of friends. Both of us with partners, manly, completely heterosexual. In private, he was my macho and I was his female.