I Dressed as a Woman and Discovered Another Kind of Pleasure

My real name doesn’t matter. Use Rodrigo; it’s generic enough. I’m 57, retired, married for more than two decades, and never in my life had I questioned what attracted me. Women. Always women. Some outside the marriage too, if I’m honest, though that’s another story and has nothing to do with this one.

Retirement gives you something you don’t expect: time. Not to rest, but to think. To explore corners you used to breeze past because you were always in a hurry. During my active years I was a competitive swimmer and went on to represent my region in national tournaments, and that pace of training and work left no room for anything that wasn’t immediate. When all of that ended, I suddenly had whole afternoons with nothing to fill them.

It was during my first winter as a retiree that I began aimlessly browsing the internet at night. My wife went to bed early. I stayed up with my laptop and a cup of chamomile tea, and one day, without quite knowing how I’d gotten there, I ended up on a forum of stories about cross-dressers and people who wore women’s clothes.

I closed it immediately. Then I opened it again.

I didn’t feel revulsion or immediate attraction. I felt curiosity, which is something entirely different. What caught my attention wasn’t the photos but the texts: people describing the feeling of putting on women’s clothing. The texture of the fabric against the skin. The weight of earrings. The way makeup changed their perception of themselves. There was something in those descriptions that hooked me in a way I couldn’t explain that night.

Over the following weeks I went back several times to that forum and others like it. I read stories, comments, experiences. No one who knew me would have imagined it from the outside: a nearly sixty-year-old man, still athletic, with an orderly life and no upheavals. And yet there I was, reading about cross-dressing with the same concentration I used to devote to swimming techniques.

***

The opportunity came when my wife went to stay with her sister for ten days. I had to remain at home because of something to do with the residents’ association, but by the third day I’d sorted everything out and found myself with an entire week and no one in the house.

I went to the hypermarket. I bought the usual: vegetables, fruit, pasta. And in the underwear aisle I picked up three plus-size thongs, tucked them between two bags of rice, and put them on the conveyor without looking at the cashier. I added a red lipstick and a navy-blue eyeliner pencil.

I drove home with my headphones on and my mind almost blank. I say almost because there was something humming beneath my thoughts, like a motor someone had switched on without asking my permission.

As soon as I shut the apartment door I locked myself in the bathroom. I pulled down my trousers, took off my briefs, and put on one of the black thongs. The fabric was paper-thin, barely a strip of synthetic lace that wedged itself between my buttocks and a too-small front pouch that held my cock tightly upward, the tip peeking above the elastic. The friction was electric. I was hard within seconds, and the glans, pushed against the fabric, began leaking a clear drop that left a dark stain on the lace.

I stood in front of the bathroom mirror for quite a while, with my cock outlined over the thong, throbbing every time I took a deep breath. I ran my hand over the fabric, squeezing the bulge, and felt the moisture of pre-cum soaking the lace. I brought my fingers to my nose, smelled them, and was surprised at how much I liked recognizing my own scent mixed with that of the new fabric.

Then I painted my lips red. I lined my eyes in dark blue. The result was obviously that of someone in disguise, but I didn’t care. What mattered was the feeling: the way the thong rubbed my cock and my hole every time I moved, the pleasant oddity of seeing myself in makeup, the tension that had settled into my belly and wouldn’t let go. I opened my mouth in front of the mirror, stuck out my tongue, dragged it across my red lips, and for the first time in my life imagined another man’s cock entering between them. Instead of frightening me, the idea made a low gasp slip out of me.

I remembered what I’d read about anal sex. I had never practiced it, actively or passively. In my sex life I’d always been very conventional in that respect. But the combination of what I was doing that afternoon and what I’d been reading for weeks led me to a simple conclusion: it was time to put something up my ass.

I went to the kitchen still wearing the thong, feeling the back strap saw between my buttocks with each step. I picked up a medium-sized carrot, washed it well, coated it in olive oil until it dripped, and went back to the bathroom. I pulled the thong down to my thighs, squatted over the bathtub, braced one hand against the wall, and with the other brought the carrot to my crack. I rubbed it first on the outside, feeling the oil slide between my buttocks and down to my balls, and then I began very slowly, from the thinnest tip.

The sensation was immediate and strange. The sphincter gave way with the tiniest pinch, and the first inch slid in almost by itself. It didn’t hurt. There was an initial resistance that eased calmly, and then something I hadn’t expected: pressure on an inner point that made me exhale slowly, almost involuntarily, a groan that sounded rough in the bathroom’s silence. I pushed a little more. The carrot went in another couple of centimeters, and my cock, still pointing at the ceiling, began dripping pre-cum onto my thighs.

It took me several minutes to get halfway up the carrot, going in and out without rushing, pulling it almost all the way out and then slowly sinking it back in, and every movement added to what I was already feeling. My other hand went to my cock on its own. I gripped it hard, fist closed, and started jerking off at the same rhythm as I was fucking myself with the carrot: when I pushed it in, my hand went down; when I pulled it out, my hand went up. Within seconds my thighs were trembling.

I finished standing in front of the mirror, with lipstick smeared, eyes half-closed, and the carrot still halfway inside me, shooting thick jets of semen against the glass, watching myself cum with painted lips and unable to stop moaning, in less than two minutes.

***

The next day I did it again more calmly and with a thicker carrot. This time I lay down on the bed, put a cushion under my hips to lift my ass, spread my legs, and took the time needed to adjust to the girth. I slathered my hole with olive oil first using two fingers, pushing them in and twisting them until the entrance was loose and slippery. I felt my own fingers sink in to the knuckles, and that sense of having my ass opened from the inside made me harder than I’d ever been.

When I replaced my fingers with the carrot, the tip went in without resistance. There was a moment, when I reached the widest part, when I felt something I couldn’t identify: a kind of internal pressure that wasn’t exactly pleasure but wasn’t discomfort either. It was something else, between the two, something that had no name in my previous experience. I pushed a little more, clenching my teeth, and suddenly the sphincter gave way and the whole carrot sank in until I felt the leaves brushing my buttocks.

A long moan escaped me, almost feminine, and even I was surprised by it. I stayed still for a few seconds, filled up, with my legs spread wide, breathing through my mouth. My cock, untouched, throbbed against my belly, leaking shining strands of pre-cum that gathered in my navel.

I started moving it slowly, adjusting the angle centimeter by centimeter, pulling it almost all the way out and pushing it back in with a firm thrust. I tilted it toward my belly until I found that spot some of the texts I’d read called the prostate, a place I’d never had any reason to look for. When I found it, I froze for a few seconds, processing what I was feeling. It was as if someone had flipped an internal switch. Every brush of the carrot against that point made me clench my thighs and let out another moan.

There it is.

I began fucking my own ass, with my free hand on my balls, squeezing them gently, without even touching my cock. The carrot went in and out, in and out, sloshing in the oil, and with every thrust my cock jolted against my belly. In less than a minute I felt the orgasm rising inside me, not from the balls as always, but from deeper down, from that point I hadn’t even known I had. My cock shook on its own and shot four thick spurts that landed on my chest, my neck, one even on my chin, without my hand ever brushing it.

That time I didn’t need any help from my hand. It was the first time in decades that had happened.

I’d had the idea of taking photos. I’d bought a cheap phone stand and placed it on the dresser, aimed at the bed. That night, on the sofa with a glass of wine, I spent a long time looking at the photos. I had trouble recognizing myself. Not in a negative way: it was more than that. It was like looking at someone who had always been there and was only now beginning to introduce himself. In one of the photos you could see me with my legs in the air, the carrot buried to the hilt and my mouth open mid-groan. I looked at that one three or four times in a row.

***

A few days later I went out to buy more clothes. I had the thongs and the makeup, but I wanted more. Black fishnet stockings, the kind that had always turned me on when I saw them on a woman. A skirt. Costume jewelry.

I found the stockings at a department store, in the lingerie section. I took them without hesitation, in the largest size available. The skirt was trickier: I ended up buying a tennis skirt in a sports shop, cutting it shorter with scissors until it fit just right, just above the knee, black and fairly tight.

Shoes were the biggest problem. I have big feet, size forty-four, and there isn’t much choice in heels in that size. I found some backless pumps in a secondhand shop, red, with a two-inch heel. They weren’t perfect but they would do.

I bought the bra and garter belt in a lingerie shop downtown. I went in looking determined, said it was a gift for my partner, and the salesman never looked up from the counter. I left with a brown paper bag and my heart in my throat, but I left.

***

I devoted the following weekend alone at home to the full session.

I started with makeup: foundation, red lips, eyes lined in dark blue. A scarf tied around my head to gather my hair. Long gold-toned costume earrings, a necklace. The bra with improvised stuffing made from old rags my wife kept for cleaning. The black garter belt over my hips, the fishnets clipped to the four fasteners, the black lace panties with the elastic fitting high on my thighs.

The skirt. The red shoes.

I stood in the middle of the bedroom for a moment before walking up to the large mirror on the wardrobe.

What I saw wasn’t perfect. It was obvious I was a man over fifty in women’s clothes. But between the stockings and the garter belt there was a triangle of white skin that the lace of the panties framed in a way that was anything but ridiculous. It had something to it. A visual tension I hadn’t anticipated. My cock, already hard, was outlined against the black lace of the panties, pushing the fabric forward like a tent, and a dark stain of pre-cum showed exactly where the glans was pressing.

I spent two hours taking photos and videos with the phone in its stand. I moved around the living room, sat in the armchair with my legs crossed, letting the skirt ride up over the garters, leaned over the table with my ass pushed out, recorded a close-up of me pulling my panties down in front and taking it out, long and hard, between the lace and the garter belt. I jerked off slowly for the camera, squeezing my balls with my other hand, and tucked it back into my panties without cumming. I wanted to hold out. I recorded different poses, different combinations of clothes. The erection never went down once.

When I returned to the bedroom, I chose the biggest carrot I had. One that required patience and oil and slow breathing. I lay down on the duvet with the garter belt and stockings on, and nothing from the waist down, with the red shoes still on my feet. I spread my butt cheeks with one hand, aimed with the other, and began to push. Oil ran down my thighs, soaking the garter belt’s lace. It took me a quarter of an hour to get where I wanted to be. The carrot went all the way in, and deep in my ass I felt a different pressure, deeper, fuller.

This time I found the right angle from the start, and the pressure on the prostate was constant and precise. I started fucking myself hard, without fear, pulling it almost all the way out and then shoving it back in with a firm thrust that made me bounce on the mattress. My thighs were shaking. I closed my eyes and imagined it was a man doing it, someone behind me, gripping my hips with the strong gloved hands of a guy who knew what he was doing. I moaned out loud, unable to control myself, my voice broken. I came over the fishnet stockings in long spurts that splattered the fake nipples of the bra.

Five minutes later, still hard, I started again. The carrot was still inside. With my other hand I grabbed it, slick with my own semen, and jerked off using it as lube. The second orgasm took longer but was deeper, almost painful, and it came out so thick it smeared my chin as it dripped down on me.

It was the first time in many years I’d come twice in a row.

***

There’s one more thing I discovered that afternoon. I had an old knee massager from when I used to compete in swimming, with three rounded heads vibrating at different intensities. I’d stored it in a drawer in the closet and hadn’t used it for years.

I took it out. Turned it on. Brought it closer.

The result was so immediate it surprised me. One head I pressed directly against my hole, still loose and slick with oil, the other two against my perineum and my balls, the vibration spreading inward in waves I couldn’t control. My cock, once again hard against my belly, started jerking on its own, twitching, spitting pre-cum without my touching it. I clenched my teeth, cranked the intensity up to maximum, and in less than a minute a third orgasm slipped out of me, this one drier, almost furious, my legs closing of their own accord around the device.

At that moment I understood that I had two different tools that worked in different ways, and that I still hadn’t tried using them at the same time. A carrot buried deep and the massager vibrating on the perineum. Something to save for next time.

***

Several months have passed since that first afternoon with the thong and the lipstick. I have a drawer in the workshop —my territory in the house— with everything I’ve accumulated. The stockings, the garter belt, the red shoes, the makeup. A bag at the bottom with more than just carrots: a life-size silicone dildo, with pronounced veins and thick balls, and a fist-sized plug for long afternoons. But that’s another story.

I’m still the same man I always was. I go swimming three mornings a week. I have dinner with my wife on Fridays. I meet the same friends as always on Sundays. Nothing I do alone changes that, at least not from the inside.

And from time to time, when I have the house to myself, I open the workshop drawer.

What I still haven’t worked out is whether someday I want more than what I do on my own. If I want a real man. Someone who’s there, who spreads my legs without asking permission, who thrusts his cock into my mouth all the way to the back and makes me swallow it, who fucks my ass, pinning me to the mattress without letting me direct a single movement. Sometimes I think about it, skirt on and lips painted, while I push the carrot all the way in. I don’t rule it out. I would never have said that two years ago.

I never would have imagined writing this either. I’m not even entirely sure why I’m doing it. I suppose there’s something about telling the truth, even anonymously, that eases a weight you didn’t even know you were carrying.

This is my story. It’s true from beginning to end.