My Transvestite Friend and I Invited a Stranger

Damián was thirty years old and, ever since he was a kid, he had felt the urge to dress as a woman. In his home it was never spoken of, so he learned to hide it like a shameful treasure. When he finally became independent and moved two hundred and fifty kilometers away from his parents, he went out with a couple of girls more out of habit than desire. The truth was different: he preferred to lock himself in his apartment, put on a skirt, and feel, for a few hours, exactly what he was inside.

That was how the years went by, and for Damián that was enough. Sometimes he chatted with men who wanted to see him turned into a female, or with others who shared his tastes, men who, in private, dressed and behaved like women. But fear always weighed more than desire, and he never met up with anyone. Until he met Rubén.

They were the same age, both single, both with lives so similar they seemed copied word for word. They were almost the same height, with delicate features and hairless skin, the sort of men women found handsome and who took advantage of that to feminize themselves with makeup. Damián had tanned skin, light brown hair, and almond-colored eyes; Rubén was pale, blond, and gray-eyed. Both wore their hair short.

When they met in person, they were nervous, like on a first date. But that nervousness dissolved almost at once, because for the first time they had someone like themselves right in front of them. They ended up at Rubén’s place. There was no sex: they discovered that both of them felt like women completely, and the idea of touching each other as men did not work between them. What did work was dressing up, putting on makeup, and behaving like the females they felt themselves to be.

From that day on, everything changed. Or rather, it changed for “both” of them. Damián went to Rubén’s place, or Rubén to Damián’s, and in those moments they were two women. They went shopping together, discreetly, with not a single gesture to betray them, saying the clothes were for their “wives.” Then they tried them on at home: panties, garters, short dresses, heels, long wigs. They made up for the lack of sex by masturbating in front of each other, looking and smiling, aware that this was the closest they had ever been to a man.

***

Over time, a new game was born: chatting with men while they showed off in their sexiest outfits. They turned them on, made them beg, and in the end they never took the next step. It was easier to stay on the screen.

One afternoon Damián arrived at Rubén’s place, who in that intimacy called himself Romina, Romi. She was already at the computer, hair done and makeup on, wearing a black lace set. Damián, who in that world was Daniela, Dani, got dressed quickly, put on the curly wig, and poured two glasses of brandy while Romi told her that she was talking to a guy around twenty-nine years old. He loved what they were, she said, and wanted to meet them.

His name was Iván. He was short, thin, with black hair and glasses; he was more than fifteen centimeters shorter than them. Even so, the two of them looked at him with a certain mocking superiority: they were taller than him, they had model legs. After a lot of insisting, after seeing them pose in their lace bodysuits and stiletto heels, Iván managed to get them to invite him to Romi’s apartment.

The truth was they agreed for two reasons. The first was that, being shorter, he represented no danger. The second, which neither of them admitted out loud, was that that night they were hotter than usual, and they took it for granted that the boy would get scared when he saw them in person and leave. Then they could end up as always: masturbating together before bed.

Romi sent him the address at eleven. While he was on his way up, the two of them changed out of their bodysuits into short spaghetti-strap dresses: deep red on Romi, pastel blue on Dani, both leaving half a thigh bare above black lace stockings. When the intercom buzzed, they looked at each other doubtfully for a second before letting him in.

He knocked on the door. The two of them blushed like schoolgirls. Romi put her hand on the handle, turned it, and opened it.

***

Iván stifled an expression of amazement when he saw them. Dani thought about how turned on she was: it was the first time a man had really looked at them, in person, dressed as women. She still wanted the guy to chicken out and leave, but something in his gaze was already starting to undo that plan.

—Come in, Iván —said Romi, breaking the ice with the soft voice she had spent years perfecting—. Welcome. We’re Romi and Dani.

—Whew. Hello, gorgeous —he replied, already more relaxed, with obvious enthusiasm—. You two are absolutely to die for.

Something awakened in both of them at those words. Without realizing it, their smiles widened. They walked in front of him toward the sofa, swaying their hips, feeling his eyes roaming over them. They served him a beer with ice, happy to take on their role, and sat on the other side of the glass coffee table.

—I’m going to be honest —Iván said after the first sip—. I’ve had several lovers, almost all of them passive, because I’m completely active. But what I’m really into is exactly this: men who feel like women and want to be treated like such. I’d never seen it in person, and I’m telling you from the heart: you’re gorgeous. Two amazons. I think I just hit the jackpot.

The two of them smiled, truly happy. The conversation grew warmer as they lost their nerves. He addressed them in the feminine, took an interest in them; he said he was a programmer and lived alone. And they, without thinking, moved and gestured like the women they were in that room.

—And... about what you said in the chat —Romi ventured.

—I’m looking for something steady —Iván pushed his glasses up with his index finger—, but without living together.

—And wouldn’t two of us be too much for you? —she pressed, with a sharp smile.

—I don’t know. We’d have to try —he stood up abruptly—. I need to take a shower.

***

Iván took a towel out of his backpack. Dani got up to guide him to the bathroom while Romi watched them. The walk was short. Dani turned on the light and stepped aside.

—It’s here —she whispered, head bowed.

—Thanks, gorgeous.

Before she could leave, he gave her a firm smack on one ass cheek and closed the door. Dani went back to the living room with her face burning, breathing hard, reliving the slap over and over. She had liked it. She had liked it so much that she felt ashamed to admit how much she wanted another.

—What do you think? —Romi asked when she sat down beside her.

—I don’t know. I don’t even know what we’re doing here with him —she looked away, unable to confess how horny she was.

—Well, I say we fuck him and give him some excuse tomorrow —Romi decided—. But I need to do it today. I’m burning up, Dani.

—If that’s what you want...

The bathroom door opened. Footsteps in the hallway made their hearts race. Iván reappeared with tousled, damp hair, finishing adjusting his glasses, wearing only a black brief. Without giving them time to react, he stopped in front of them and pulled it down.

The two of them looked up. First the messy hair that gave him a sexy air, then that smile of someone who knows he’s in charge. And finally they lowered their eyes to his sex: different from theirs, much thicker, and although flaccid it was already as long as theirs were when fully hard. Both of them shivered imagining his full size.

Iván placed his hand on Dani’s head and, gently but without hesitation, brought her closer. She opened her mouth by pure instinct.

—That’s it, that’s how I like it —he murmured, guiding the rhythm—. Slowly, suck it properly.

Dani felt it growing inside her mouth until she could barely fit it. Romi bit her lip, jealous to see her friend having her first taste. When he was fully hard, Iván pulled it back: there stood that huge cock before them, almost twenty centimeters.

—Now you, gorgeous —he tilted his hips toward Romi.

—Yes...

Without needing to be held, Romi closed her eyes and took it into her mouth, still smeared with her friend’s lipstick.

—Are you sure this is your first time? —he savored the motion—. You suck it like an expert. Just like Dani.

***

The two of them coordinated without meaning to and sucked him together: Romi on the glans, Dani devoted to his balls with long licks. But Iván pulled them away soon enough, taking them by the hair. The party was only just beginning.

—I want you both on all fours on the sofa, facing each other —he ordered—. Today I’m going to take good care of you.

They obeyed instantly. They ended up face to face, their little asses in the air. Iván took a tube of lubricant out of the backpack, spread it on his fingers, and brought one hand to each of them. He moved their panties aside, caressed them, and started working them from behind, first one finger, then two.

—What well-behaved little sluts —he said, pleased to find them clean—. And eager.

—It’s just... we like to be clean for you —Romi murmured, barely a thread of voice.

In the two of them’s muddled heads, only his words could fit anymore. They took his cock back into their mouths, coordinated, lost in desire, no longer holding back their moans while Iván’s fingers slowly stretched them open.

Then he pulled them apart again. He took Romi by the hip, arranged her face against the backrest, and lifted her ass up in front of his saliva-slick sex. She clung to the sofa and looked over her shoulder as she was about to lose her virginity.

—Wow, you’re very tight —he murmured, pushing carefully.

When he went all the way in, Romi let out a scream and arched her back. The initial pain gave way to pleasure, and soon she was pushing her hips herself to spear herself on him.

—I’m your girl, Iván! —she roared, beside herself.

Dani watched her, dazed, moaning, writhing, shouting what she felt, until Romi came and stained the front of her panties just as he drove into her deepest.

—This one’s been broken in now —Iván gave her a slap—. I’m going to wash up. Then it’s your turn, gorgeous. Come here.

***

He didn’t wait for an answer. He took Dani by the hand and led her to the bathroom, where he sat her down in front of him and offered her his cock again, which was regaining its hardness with every stroke. Then he hugged her from behind back into the living room, rubbing his sex against her ass and pinching her nipples through the dress, his body pressed to hers.

He let himself fall onto the sofa and lowered her slowly to impale her right there. Dani’s little ass offered more resistance, took longer to open, but finally yielded as she let out a long moan.

—God, yes! —she rode him from behind, guided by his hands.

—You’re tighter than Romi —he growled.

Now it was Romi’s turn to watch her friend being broken in, to hear her scream that she belonged to him, to watch her come apart with pleasure until she reached climax. Dani ended up on the floor, legs spread, trembling.

What followed was a long night. Iván used them in turns, mixed them together, made them come again and again, doling out orders and slaps while they competed to please him. When they no longer had any strength left, he knelt them together, cheek to cheek, and jerked off until he emptied himself over both their made-up faces, leaving them with smeared mascara and idiotic smiles of satisfaction.

After that, the three of them showered. They took off their wigs, naked, while he fondled them to his heart’s content. They made up the sofa bed like two housewives, opened a few beers, and lay down beside him to watch TV, one on each arm, holding him like the lovers they had become. Before sleeping, he kissed one and then the other, devouring their mouths, and took them again until sleep overcame them without even washing their faces.

***

—Good morning.

—Hi.

Damián and Rubén got up that Tuesday with their bodies wrecked and their spirits sky-high. They showered, had breakfast, and, as two ordinary men again, went off to work in opposite directions.

Throughout the day they exchanged messages, reclaiming their identities as Dani and Romi on the phone screen, remembering everything that man had given them. They quickly came to the same conclusion: they couldn’t let him go. They wanted to spend as much time with him as possible, dressed as women, acting like his girls.

As soon as they left work they met again at Rubén’s apartment. They got dressed for hours: tight black dresses, platform heels, wigs in their natural shades gathered into high ponytails, the same crimson lipstick. They lay down on the sofa bed and sent him a photo. The reply was not a message, but a call.

—Hello, gorgeous. How are you both?

—Horny —Dani replied—. And we want you to take care of our little problem. Feel like it?

—I’d love to take care of my girls whenever I can. If you’re interested in being that.

—Of course we are! —they answered in unison.

—Have a good time, let me make you mine again and again, teach you to be my favorites. Interested?

—Yes... —Romi murmured, already with her hand between her legs.

—Then I’ll see you in a bit. Are you still at Romi’s place?

—We’re here.

He didn’t take long to show up. When they opened the door, Dani and Romi were waiting with their hands behind their backs, looking up at him with a desire they no longer tried to hide. They practically dragged him inside and, as soon as they closed the door, they knelt at his feet, lifting their eyes to him with genuine devotion.

—Then let’s begin —said Iván, pulling down his pants.

That man had found his two girls, and those two transvestites had finally found their stallion.