The Autogynephilist

Since childhood I have held dreams inside me, often for years but, in truth, somehow they never seemed to slip out into real life — at least that was until the day I saw her on the train.

Let me tell you more…I had worked late in the office one evening to finish a report and my manager gave me a mid-week day off as reward. Rather than sit alone in my apartment on a rainy nearly spring day I took a train to Saltash Art Museum - the 09:47 in order to avoid rush hour. I had the carriage to myself until Sutton-on-Water when a woman opened the door and sat on the opposite side of the carriage with her back to the direction of travel. 

Over the top of my book my eyes greedily took her in from her shiny shoulder length hair to the heels she wore. In my head I imagined she was a successful professional in some unimaginable field like computers or fashion. The train was ten minutes out of Sutton-on-Water when she stood and took off her winter coat revealing an unseasonable summer dress. She carefully folded her coat and placed it on the adjacent empty seat then smoothed her dress under her before sitting back down. 

She took a mobile telephone from her purse began swiping at the screen completely unaware of my eyes searching out details that I may have missed the first time, discreet makeup, striking matt deep burgundy lipstick that matched perfectly with her nail polish and purse. As the train rocked the hem of her mid-thigh length dress gradually rode up slightly revealing the darker top of her tights. The motion of the train then revealed my mistake as gradually a suspender and a couple of millimetres of bare thigh were revealed. 

Without my realising it I had allowed my book to sink down onto my lap as I waited for the trains motion to reveal more upper thigh. Her eyes flicked up from the phone catching me staring, she blushed as she followed the direction of my eyes then unhurriedly smoothed the hem of her dress back into place. I quickly lifted my book and pretended to read even though I could not concentrate, I was certain I could still feel her eyes on me daring me to look again. 

She was back to looking at her phone when I next glanced up then, as if her super power was an ability to hear the movement of my eye muscles, she openly looked at me and smiled. It was my turn to blush and to my horror I began to feel a stirring below the waist, the train began to slow for the bend just before Sutton Halt Station. 

Her deep burgundy polished fingers danced across the phone and she held it to the side of her face “it’s Roger” she said “my train is just coming into Sutton Halt Station, see you soon” her voice just loud enough it seemed to ensure my hearing it.

I was in turmoil as, inside my head, eyes argued with ears each demanding they were right. I slowly lowered my book to conceal my cock which had no interest in rightness as it tented out my pants.

‘Roger’ took a compact from his purse and needlessly freshened his immaculate lipstick moments before the train began braking. I had seen drag artists online and read stories about men who dressed as women but actually seeing a woman who was a man on the inside in real life had taken my dreams to a whole new level. Roger smiled as he stood and put his coat back on, neither of us felt any need to pretend disinterest, the train door opened he gave a little wave and was gone. 

Inside my head I spent the rest of the day as my own version of Roger. While I walked around Saltash Art Museum it was as if my ears could hear the click of my heels on the marble floors. As I walked to a café for lunch I could feel the hem of my dress being gently blown against my thighs in the breeze, hear the swish of my stockings. As I sat in the café I imagined the feel my stockings tugging at my suspenders, the tug of my bra strap as I put a fork of food to my burgundy lips. I kicked off my imaginary heels under the table and felt temporary relief.

I even felt the hot, tightness as I slipped my feet back into the imaginary heels before heading to the restroom to take myself in hand for the third time since arriving in Saltash.

———//———

I had been awake since before six, usually on a Saturday I would sleep in until lunch but this was no usual Saturday. Last pay day I went online, not that I like shopping online but it was easier to shop on Marks & Spencer website than go into a store. I had been watching from my window for a couriers van for two hours and fifty three minutes when it finally arrived, I heard the lift door open followed by a loud bang on my door.

The courier was smiling, did he know I wondered, was the bastard smirking at me? My excitement was building as I carefully felt the bag, surely he could not have identified the contents by feel alone. I had paid extra for Saturday delivery and now with the whole weekend before me I was shaking, opening the packet would set a dream free that had lived within me for years.

I had read enough online since seeing Roger to know exactly what I wanted and had researched enough sizing guides to have some confidence that I had selected sizes that would fit me. Not for me the flimsy lace lingerie that modern women wore, my heart had always longed to surrender my body to the control of proper foundations. 

Perhaps that was where it all started, in my mothers mail order catalogue, I remember at the start of the underwear section each year it said ‘every woman deserves the confidence that only a proper foundation can give’. 

There was so much more I had wanted as I had browsed the Marks & Spencer website - dress, shoes, stockings, makeup - I would buy something each month with my spare money I decided…and even though I knew that I would never leave my apartment at least I would be able to imagine what that would feel like. 

Despite my apartment not being overlooked and on the ninth floor I closed the curtains in my bedroom before opening the packet, turned on the light then lay out the contents on my bed first examining the high waist panty-girdle. What I had read online confirmed a panty style would be better to ‘hold everything in place’ I could feel my cock throbbing as it struggled to fully harden inside my trousers.

The matching bra came in a box, I had chosen it as much for the website description as anything else, the website listing described it as a ‘total control bra’. That was exactly what I wanted - to have my body totally controlled. 

The little same colour embroidery details on the bra matched those on the panty girdle perfectly and another phrase from the mail order catalogue sprang to mind - ‘nothing feels more feminine than matching underwear’  it always said at the top of the pages of matching lingerie sets as if wearing a non matching underwear was a fashion crime with undefined penalties.

Inside my head I had fantasised over this moment for years and now my fantasy was actually going to happen in the real world there was no reason to rush. First I took off all of the tags, the bra out of the box and put them in the shredder along with the order paperwork. For some guilty reason I was certain that someone would see inside my trash bags and strangers would point at me in the street. I needlessly showered again and as I showered I thought about what I was just about to do and immediately my cock hardened. 

My excitement coupled with anticipation as I came were replaced with feelings of shame, then guilt swept over me…what was I thinking? A fantasy that existed safely inside ones head was one thing but actually buying myself a bra and girdle was just wrong…what would my mother say if she were still alive?

With just a towel around me I looked down at the bed feeling ashamed of myself. 

It was not too late, I could throw them away, no harm had been done, I mean I hadn’t worn them…not even tried them on…barely even touched them. An in head fantasy, for that was all it was, had not yet become a real life perversion. 

Growing up we had not been a wealthy family and my parents hated waste but how could I send this bra and girdle back - I had shredded the receipt, pulled the tags. Dressing in joggers and a Tee I turned out the bedroom light and closed the door behind me blocking out the guilt I felt.

Shame did not subside until mid afternoon. It would be ridiculous to spend all of a whole months spare money and not even try them on just once I reasoned. 

Just once. 

That is all - once won’t turn me into some sort of a crossdresser and it would prove to me once and for all how wrong a man wearing women’s clothes is. Then I would throw them out, it would be as if it never happened.

Panties first, bra second the survey on mums-net had said was most poplar order of dressing and therefore the right way to dress. Who was I to argue, plus as I will only get one chance I may as well do it right. I stepped into the panty-girdle and went to pull it up like underpants, as I struggled to pull it up I began to think it too small but once I had it over my hips and my cock tucked back between my legs the rest was easy. I tugged it up and then up some more, bent over, sat on the edge of the bed, stood, paced back and forth. It felt unsettlingly good, I could feel my cock straining without success. The girdle had my cock under control, had me under control in a very nice way. I began to think of wearing the bra and girdle for a while, perhaps until bed time would be OK…I would be glad to take them off by then, of course I would.

After pulling the fat of my chest out of the top of the girdle it looked like I had little titties hanging there on my chest. I picked up the ‘total control’ bra, slipped my arms through the straps and, like women on mums-net who said it was the right way, I leant forwards to ‘settle my breasts into the cups’ even though all that I had was a little fat.

Fastening a bra was much harder than I had imagined, I wriggled and turned from side to side trying to fasten the bra while trying to keep my little manboobs in the cups and straps over shoulders. Trying to couple hooks with eyes behind my back required a skill set that I did not possess. “Oh no…oh no” I said to no-one as I felt myself becoming over excited. With my cock contained inside the panty girdle there was nothing I could do to stop events from running their course. The mirror I showed I was still holding the ends of the unfastened bra behind my back as the point of no return passed, then a seemingly never ending orgasam kicked-in with an intensity such as I had never felt before. 

Just as intense as the preceding pleasure an equivalent level of shame consumed me. 

This was not my plan…cumming while crossdressed was so much worse than just trying the clothes on. Why had my cock turned it into a sexual thing. And why was it so intense? I threw the bra back onto the bed, glanced in the mirror at the little man-titties that hung over the top of the girdle and turned away as I began struggling out of the high waist panty.

Since the day I saw Roger I had been masturbating so much that there was barely a damp patch in the girdle, but enough to provide proof, as if any proof were needed, that not only had I worn it but, intentionally or not, I had masturbated while wearing it. “But at least I did not actually wear the bra” I whispered to myself by way of reassurance “and, after all, a panty girdle is just like tight underpants”. 

I shoved the bra and girdle into a black trash bag and hid it under my bed. On Wednesdays our apartments trash was taken away, I would sneak my bag of shame into the dumpster just before it was emptied then it would be as if it had never happened. 

Inwardly I smiled as I thought how by summer I would have completely forgotten all about the underwear episode. 

 

———//———

Leaning forward I settled my little manboobs into my total control bra then quickly fastened the back before doing what I had learnt was called ‘the scoop’ which simply meant repositioning underarm fat into my bra cups. I smiled as I turned side to side and thought of that saying about making mountains out of molehills, my total control bra certainly did that. I took my new summer dress from its hanger on the closet door and slipped it over my head, did a little shimmy and felt the hem settle reassuringly at mid-thigh.

Stepping up into my heels I walked to the bathroom to put on my favourite deep burgundy matt lipstick, a perfect colour match to my nails. I carefully checked every detail in the mirror. “Perfect” I said quietly as I felt my cock straining against the gusset of my high waist panty girdle. 

I lifted the hem of my new summer dress and released my cock. A couple of strokes brought me to full-on hard. My heels gave me enough height to be able to cum into the washbasin while watching in the mirror. How handy is that? I began to slowly stroke, moved my shoulders slightly and felt the tug of my bra straps, swayed a little and felt a reassuring tug of stockings against suspenders. 

After wiping the last drips on a tissue I settled my cock into its controlling prison and smiled. Nothing to be ashamed about, autogynephilia is my hobby and everyone needs hobbies. 

I checked my watch, slipped my new iPhone into my purse, time to leave - my train to Saltash is at 09:47, a new exhibition opens at the Art Museum today,,,

———//———