The Bachelor Party Where I Was the Gift

I want to write this now that I have a little free time, because later you never know when you’ll get to sit down and tell it again. Those of you who follow me already know I live with my older brother and that we ended up as a couple; I also told you how my transition began and who stood by me through the whole process. What I’m going to tell you happened right in the middle of hormone treatment, when my body was just starting to become the one I had always wanted.

Those were strange and beautiful months at the same time. I looked in the mirror every morning and discovered something new: the curves that were starting to show, the softer skin, the way clothes were beginning to fall differently on me. I felt like I was finally inhabiting my own body, and that gave me a confidence I had never had before. I walked out into the street with my head held high and I liked it when people looked at me.

My two brothers worked all day. Besides being good men, they were responsible and true to their word, and from time to time they brought friends home. A lot of them saw me passing by, of course, but seeing is one thing and knowing is something very different. One day I was keeping a sensible distance when I heard one of them daring to say:

—Your little sister is very pretty.

I burst out laughing. It was lovely to hear that from someone I barely knew, and the others played along with soft compliments. It made me feel good, unexpectedly.

Time passed, and one afternoon one of them asked whether I had a boyfriend. My brothers answered no, that the thing was I had a secret. The others fell silent, intrigued, until the eldest said it bluntly:

—The thing is, let’s say Sasha used to be Santiago.

A strange silence fell. The usual questions started, the kind that mix curiosity with a little bewilderment, and my brothers calmly explained my whole transition to them. None of them got up from the table. For me, that was already a lot.

With time, I started joining their men’s gatherings. That was what they came home for: to drink beer, eat something, watch football, and talk about their things. I dressed up as always, in a short skirt and with my hair neatly done; back then I wore it halfway down my back, cut in layered, feathered pieces. One of the friends looked at me and said:

—Hey, cutie, want one?

—I don’t drink —I told him—, but I’ll keep you company with a soda.

So that afternoon went. Out of nowhere my brothers put on music and we started dancing. Picture the scene: me moving among so many men, feeling the heat of their looks. I got turned on, I admit it, the tips of my tits hardened against the fabric and I noticed my ass getting wet just from imagining any one of them opening my legs right there, but I held myself back. I knew my brothers’ friends by sight, not personally, and I didn’t want to get ahead of myself.

Those gatherings were repeated several times. I learned to move among them naturally, to joke, to return the compliments without overdoing it. I enjoyed the game of knowing myself desired and at the same time untouchable. I noticed how some of them followed me with their eyes when I got up to fetch more sodas, how the bulge in their pants showed when I bent over on purpose, and how they lowered their voices when I came near. That little power pleased me more than I was willing to admit.

***

One day my brothers surprised me with a proposal. They asked me what I thought about giving one of their friends a bachelor-party show. I froze. I could have imagined it from them, but not from an almost stranger. I had already been with other guys, though always people I knew, people I had some level of trust with.

—Does he know what I am? —I asked—. And what I have with you?

—He knows everything —they told me.

I thought about it for barely a second and said yes. They told me when it would be, that they would be there, some friends I had already seen once or twice, and, of course, the guest of honor.

In the days before, I thought of nothing else. I imagined the scene over and over, nervous and excited in equal measure. I chose every detail of the outfit carefully, rehearsed the moves alone in my room, and put together the playlist that would get me in the mood. I didn’t want it to be just any dance; I wanted them to remember that night forever.

On the appointed day I went early to the salon to get ready calmly. I asked them to style my hair in soft waves, they lined my eyes and painted my lips a deep, intense red. I dressed as a little sailor girl, with a tiny skirt and long white boots, one of the many gifts my brothers had given me. I looked at myself in the salon mirror and almost didn’t recognize myself: I was edible. When we got to the house, they honked the horn and we went in. Inside, the six friends and the guest of honor were waiting.

I got out of the car and they all whistled at once.

—Wow, how cute!

—What a doll!

I thanked them laughing and blew kisses into the air, letting myself be carried away by the welcome. The adrenaline was already running through my whole body.

I had prepared the music on a speaker. I was going to dance two songs: one for the striptease, a slow, sticky blues, and another dirtier one, with a thick bass and a funk rhythm, for the part where I would play with a dildo. Two pieces conceived like scenes in a movie. The idea was to take them from curiosity to delirium.

***

I started dancing slowly, marking every movement. I stripped off piece by piece as I moved toward the guest of honor, who never took his eyes off me. First the sailor blouse came off, leaving my tits out, held up by hormones, with the nipples hard as little pink pebbles. Then the skirt, which slid down my thighs to the floor. I was left with only the white knee-high boots and a tiny thong that barely covered my hard cock between my legs. I ran my hands over my tits, pinched my nipples in front of him, and lowered one hand to the bulge in the thong, squeezing myself so they could all see how horny I was. The guest of honor licked his lips and the others adjusted their cocks in their pants without even pretending to hide it. The first song ended with me barely covered and the room air thick, packed with contained heat.

I picked up the little bag I had brought and the second song started. I took out the dildo, a thick black one with visible veins, and brought it to my mouth. I licked it slowly, looking the guest of honor in the eyes, teasing the length with my tongue, unhurried. I ran the tip across my lips, gave the head little licks, and then shoved the whole thing down my throat, choking myself a little on purpose so my mouth would fill with spit. When I pulled it out, a thick strand hung from my chin down to my tits. Then I lowered it, pulled off my thong, and was left with my cock out, hard and dripping, and my ass wide open for everyone to see. I sucked two fingers and shoved them into my asshole to prepare myself, moving my hips to the funk rhythm. Once I had it well wet, I guided the dildo between my cheeks and shoved it in with a single thrust, groaning loudly so it could be heard over the music.

—Ah, fuck, that feels so good —I panted, biting my lip, moving my ass forward and back over the toy.

Once I had it inside, I walked on all fours through the middle of the room, the dildo buried all the way in and my cock swinging between my legs, dripping pre-cum onto the carpet.

—Fuck! —one shouted.

—Fantastic!

—Uffff, look at that ass!

My brothers were laughing, amused, watching how their friends reacted, all of them already stroking the bulges in their jeans with no shame at all. Like that, on all fours, I crawled over to the guest of honor, arching my back so the dildo would sink deeper with every crawl. I unbuttoned his pants, pulled down his boxer briefs, and took out a thick, heavy cock, already semi-hard. I took it in my mouth without thinking, sucked it down to the base in one go, felt it swell against my tongue and harden in seconds until it was like iron.

I sucked his cock eagerly, swallowing it down to the balls, pulling it out with a smack and pushing it back in. I ran my tongue over his balls, sucked them one by one, and returned to the head, pressing it between my lips and circling my tongue around the tip. He grabbed my hair and started fucking my mouth at his own pace, driving into my throat until my mascara started to run with tears.

—Take it out for me —I asked him, my voice rough, spitting out his cock, and he understood right away and yanked the dildo out of my ass with a pull that tore a long moan from me.

I climbed onto him straddling him, grabbed his cock, and slowly worked it into my open hole, feeling every inch push inward. I took him all the way to the hilt, until I felt his balls slapping my ass, and I stayed still for a second, trembling, with his whole cock clenched inside me. Everyone watched in silence, and that silence made me even hotter. I started moving on top of him, up and down, squeezing his cock with my ass ring, while he grabbed my tits and pinched my nipples.

—That’s it, bitch, keep going like that —he panted.

—Come on, cum inside me, fill my ass —I answered, riding him harder, feeling my own cock bouncing between our stomachs.

I bounced on him with all my strength, and he thrust up into me from below, until I felt his fingers dig into my hips, his whole body tense, and he unloaded inside me with a hoarse groan, filling me with hot semen that ran down my ass when I lifted myself just a little. I stayed a few seconds with him inside, squeezing it out of him with my asshole. Then I bent down and spoke in his ear.

—Congratulations. I hope your girl is accommodating; if not, you know where to find me.

And I kissed him on the mouth, slowly, while the others applauded and some already had their cocks out, jerking them openly.

***

I put on some short shorts that barely covered me and a light blouse, and we all sat down to eat dinner. There was conversation, laughter, harmless questions. They asked me about my transition, about how the process had been, and I answered with the ease of someone who had already made peace with herself. At last I gained confidence with my brothers’ friends and they with me. That night I stopped being the mysterious little sister for them and became just another one at the table.

I always say it jokingly: a man will be a man. Put a skirt on a broom and he’ll still find a way. That room was living proof of it.

But the night didn’t end there. Once we were all loosened up, my brothers and I put on a second show, this time the three of us together. They started by kissing my neck and back, running their hands over me slowly, as if we had the whole night. One sucked my nipples while the other licked my ass from behind, spreading my cheeks with both hands and slipping his tongue into the asshole that was still warm from the guest of honor. I closed my eyes and let myself go with those mouths and hands I knew by heart.

From caresses they moved on to more. The eldest lay down on his back on the sofa and I got on top of him, impaling myself on his cock in one single thrust, moaning loudly. The younger one stood behind me and put his dick in my mouth, fucking my throat at the same rhythm his brother was fucking my ass from below. They took turns fucking me too, changing my position, putting me on all fours, on my side, against the table, setting a pace that had me completely surrendered, with my hard cock dripping between my legs and my tits bouncing with every thrust.

The room had fallen silent, everyone focused on every movement, and that silence made me even hotter. I felt their eyes nailed to my skin as if they were another form of touch. Out of the corner of my eye I could see the friends jerking off on the sofa, pants lowered and balls out, watching us like it was a live porno movie.

Until at one point they took me both at once. The eldest under me, his cock buried deep in my ass, and the younger one above, forcing his into the same hole, pressing against his brother’s until they opened me all the way. Feeling both cocks at once, throbbing inside me, rubbing against each other, ripped a moan from me that I couldn’t hold back, a long, filthy howl.

—Ah, yes, like that, break me, don’t stop —I begged them.

I clenched my teeth, closed my eyes, and let myself go completely, without shame, without thinking about who was watching. They shook me between them, thrusting hard, and I came and came, spraying my own cum over the eldest’s belly without needing to touch myself.

The friends were still frozen on the sofa, cocks out, not knowing whether to keep watching or join what was right in front of them.

—Come on —I said between gasps, with the two cocks still inside me—, don’t just stand there, come fuck me.

And they came. They stood around the sofa with their cocks in their hands and I moved between them as best I could. I opened the guest of honor’s mouth and sucked his cock while the others took turns putting theirs in me. They pulled my brothers away and set me on all fours on the rug. One behind, one in front, one in each hand. I swapped them, sucked them, shoved them in. One came in my mouth and I swallowed everything; another came on my tits, leaving thick ropes that ran down to my stomach; another pulled out at the last second and shot in my face, on my lips, on my eyelashes. They filled my ass twice more, my mouth several more times, and I came over and over, jolted by so many hands and mouths. I lost count of how many orgasms I had and how many cocks went inside me that night. The room smelled of sweat, semen, and alcohol, and I didn’t care; I was where I wanted to be, given over, soaked through, and happy.

***

When everything calmed down, it was the guest of honor who stayed with me. I spent the night with him, we slept together and sought each other out again before the sun came up; he woke me by sliding it into me from behind very slowly, and we ended with him coming inside me once more, holding me tight. In the morning we each went our separate ways, but that night sealed something. To this day we’re still friends; we see each other when we can or when I’m invited, always with a knowing smile between us.

I hope to tell you other experiences later on, taking advantage of the free time I have. For now I’ll leave you with this one, which is one of the ones I remember most.

With love, Sasha.

😘