Fashioning a Fop
An 18th century tale of a trans man discovering himself through dressing in men’s clothing for the first time
Cis M/trans M (currently closeted/questioning so occasionally refers to himself as a woman). Vaginal and anal sex, roleplay, references to homosexuality/cross-dressing being illegal.
Note: I’m not a historian and this is a period setting for fun rather than accuracy! Errors are very possible.
Our village has changed significantly in the fourscore years since my grandmother’s time and my family has seen both hardship and triumph. What used to be a farmhouse in the days of the Stuart Restoration– when my ancestors worked the earth– is now an inn kept by my mother and father, assisted by my maiden aunt and I: their only daughter. I have two brothers, both grown and gone to work in the nearby town to meet the rising need for men willing to do the invisible, thankless work to support the rich men getting richer off their labour; they are sorely missed around the house by my parents while I must now do the work of three. Ah, but I ought not complain: our business is staying afloat while our neighbours struggle, their fields fallow with a lack of seeds to sow, and my brothers send back money when they can afford it.
We are positioned on the largest road to a large port town recently swollen with an influx of merchant ships and newly prosperous with newly wealthy men spending their days reading pamphlets aloud in coffee houses for their equally wealthy friends to make faces at. Through Providence our inn has become a popular respite for travellers to rest their tired bones and their dusty horses, although that is not the only mode of customer we see. The road also serves a number of other towns in the county and so our passing trade includes a variety of characters. I daresay I have met a wider range of personalities than most men in the big town, and certainly more than most ladies, who I hear are forced to spend their days sitting around a miniature lace-covered table sipping tiny porcelain cups of hot water infused with leaves that cost so much that they must keep it locked in a chest for fear the maid will skim the household supplies to supplement her income.
I tell you this to illustrate that despite my provincial background we were used to birds of all feathers. We largely catered to those passing by although occasionally we had customers who rented a room for a longer period of time– often for comfort, as a similarly priced room in town would generally be half the size with twice the occupants. There were several repeat customers who would book long in advance to be able to use their favoured room when travelling for business for one or two weeks out of the year. Then there were those who stayed for even longer.
Mr Flinn was a young man of some four and twenty years, hardly older than myself. He told us that he chose our establishment due to it being a fairly central location to several nearby towns which he visited for work. What exactly he did for work was less clear, and he changed the subject when pressed. We are not usually the type of people to pry but he is certainly becoming an object of some curiosity. He has been staying here for a little over two months now, and is perfectly charming and polite, keeping his room in good order, paying promptly and making conversation with other guests. I admit to having occasionally listened in on such talk while wiping down a table or bringing ale but he never reveals anything about his history of any significance.
His peculiarity became apparent during the first week of him staying here. When he had first arrived at the inn he was simply dressed in a travelling cloak, hair brown and bare under his hat. The first morning he left by horse along the western road he wore a grey curling periwig under a three cornered hat with a fine feather, a fancy long coat and breeches. Later that week he set off by foot in the opposite direction wearing long trousers and a rough poorly shaped leather weskit like a working man, his feet shod in wooden clogs. Had I passed him on the street I would not have known him for the same man. We have since seen various variations on these two main characters, which I have taken to thinking of as the Fop and the Farmer, and once or twice a third version wearing the dark blue jacket and wide white trouser of a sailor with a red rag tied about his throat.
What was astonishing to me was not only how different the same man could appear due to the alteration of his garb but how he held himself with an entirely different posture and even walked with an altered gait. He usually took breakfast in his room in the mornings so I had not had the chance to make a study of his conversation, but had once had the opportunity to exchange a scant greeting as I was passing the stairs and I felt certain that his very diction was changed. It led me to wonder if the pleasant gentleman who spent many evenings relaxing and playing at cards in the parlour was yet another masquerade. Mr Flinn seemed to have a local accent, suggesting a man of our own class, but perhaps that was an affectation in order to gain our confidence– although for what purpose I was unsure.
“He could be a highwayman,” my aunt Mary suggested, a brightness in her eye that implied to me that she was more intrigued by the idea than afraid.
“Whatever he may be, he pays his way and brings no trouble home,” was my mother’s no nonsense reply.
In fact he had actually brought us more business, having previously recommended the inn to other patrons. One of these was an old garrulous man who paid for a room for just one night but barely seemed to use it, mostly sitting up and drinking with a group of locals. The other was still staying here, having arrived the day before yesterday. He was paying half rate in order to stay in Flinn’s room which was not a unique situation: many travellers decided to save on money by sharing. His name was Crosby, he seemed a similar age to Flinn, and they seemed by their interactions to be good friends. I had idly considered the idea of trying to engage him in conversation in the hopes of finding out more about Flinn’s occupation, although perhaps the mystery of it was more enticing than whatever mundane truth may lurk beneath.
Flinn’s room was at the very back of the house, the last one in a line of rooms. We have now arrived in the present moment, the time in which this tale takes place. I had been tasked to fill the wash jugs and empty the basins in each room and to neaten up those rooms that were still occupied and so did not require a full turning out for a new customer. I had almost completed my job, and knocked lightly on Mr Flinn’s bedroom door even though I was certain I had seen he and Mr Crosby set out early this morning and not yet returned.
I had always found him to be a clean and orderly guest so there was not much to tidy despite the extra occupant. I took my time over my tasks, straightening the bed linens and sweeping the floorboards, so that I could also sweep my curious eyes over the items left behind.
There were two trunks: one a heavy steamer which I knew belonged to Flinn, and the other a much smaller travel trunk which must be Crosby’s personal effects for the few days he was visiting. Each room was supplied with a simple desk for those who needed to work on papers or so on, although Mr Flinn seemed to use his as a dressing table. A wooden knob on a folding stick stood upright, which I supposed was where the grey curly wig usually lodged, but I had seen Flinn wearing it this morning so it was now absent. There was a jar of wig powder; a compact of powder for the face; salves; perfumes; soaps; tooth powder; ointments; and a fine boar hairbrush, all lined up neatly on the polished wood. A looking glass was propped up against the wall, and I saw my own curious reflection peering back as I hurriedly turned away as though caught in an act of some mischief. On the bed had been lazily cast a copy of the printed score of Gay’s ‘Beggar’s Opera’ which I had never seen before but I supposed could belong to either of the two men, both seeming equally likely to be literate.
A wooden linen press was supplied to store the clothes of whoever stayed in this room and I opened it up, giving myself an air of somebody performing a duty, telling myself that I was merely checking that everything was in order. It felt important to be convinced in my own convictions even when I was in private. If I had been expecting to find anything too exciting, I was disappointed: I had seen most if not all of these clothes before. They were all folded neatly and sorted by clothing type rather than by purpose. I gazed for a moment at a shelf of shirts, a mixture of thick rustic linen and fine cotton that I felt must have been at least double the price. Some of these might be Mr Crosby’s clothes also, but he mostly dressed in an ordinary style of clothing with plain woollen jackets and unadorned waistcoats: the kind that might be worn by any man of my own social class.
I closed up the press and turned to leave. My gaze fell upon something, a small sliver of colour just ever so slightly peeking out from underneath the heavy lid of Mr Flinn’s trunk. I hesitated, arrested for just a moment by the knowledge that looking within would certainly be prying, unable to be explained away by the responsibilities of housekeeping. Ultimately, however, my curiosity could not be reasoned with, and the trunk had been left unlocked. I eased the lid open to reveal its contents, eagerly leaning forwards to examine them. It was more clothing, entirely new to me: I had not seen Flinn wear them and I had not even seen any gentleman wear anything resembling this style of clothing. The closest I had seen was reproductions of portraits that showed men who dressed in the ‘macaroni’ style, but oils and inks did not come close to representing the beauty of the items that lay before me.
The object that had been trapped in the trunk was a sleeve of a silk coat which was of a green the shade of a ripe gooseberry, elaborately embroidered in gold and pink with such a fine hand that I could not imagine the length of time taken over such work. It was so beautiful that my hands shook as I traced over the flowers and leaves which had been captured in cloth. Such a fine trim along each edge, and the gleaming buttons that lined up along the breast and down each cuff like tiny mirrors! The material itself was so fine, as smooth as water, that I found myself stroking it as though it was a living creature, petting the curve of the shoulder and allowing my fingers to dip into a capacious pocket and nestle into the lining.
This was not the only treasure to be discovered. Next was a waistcoat, cut from the same viridescent silk, beautifully sewn with butterflies fluttering across the fabric. Each small button was wrapped in silk, and I spent a pleasant moment buttoning and unbuttoning one of these purely for the sensation of it. My attention turned to a shirt, less elaborate but even I, with no knowledge of fashion, could tell that it was skillfully tailored to match the rest of the suit, and the cascade of ruffles down the front marked it out as more extravagant than any I had seen before. The breeches were a fine gold brocade, and my breath caught in my throat as I lifted them out of the trunk to see them more closely. The material shone in the sunlight, and I could not quite understand why they made me feel so dizzy as I smoothed out a crease, automatically holding them to the front of my body.
I do not remember consciously coming to the idea, only that one moment I was wondering whether I might be around the same size and shape as Mr Flinn and the next moment I had taken off my apron and was removing my gown. I kicked off my slippers and then removed my woollen stockings with their darned heels and ugly pulls in the knit. I realised then that most of my underthings could not be worn underneath a man’s clothing, so I unlaced my jumps so that I could slip out of my shift. Now I was nude from my toes to my neck, wearing only my house bonnet to keep my hair neat and covered. In the looking glass I could see my small breasts, my pale stomach, the brown curls between my legs.
There was a pair of silk stockings ready for me and even these were decorated with flowers and ribbons. They were so fine and soft that they let the light through them and as I drew them up each leg I felt a shiver of delighted luxury. The act felt truly improper, indecent, although it never crossed my mind that this was because I was dressing outside my sex. Rather, the sin I felt most strongly was that these were the clothes of a gentleman, although I reasoned that they were most probably stolen in the first place since I could not see how somebody who could afford clothes like these would be staying in our inn and gadding about on horseback or on foot.
Each stocking was carefully secured by a pink garter and then it was time for the breeches. There was no sign of drawers in the trunk: perhaps Flinn wore his ordinary drawers with this suit as they would likely not be seen, or perhaps he wore none at all. I had nothing of my own to substitute so I went bare. I pulled on the breeches, marvelling at how high they sat on my thigh, how they clung to the curve of my buttocks. They felt as though I was wearing nothing, but my reflection showed a pair of shapely legs wrapped in sumptuous golden cloth. I admit my vanity: I turned and stared, turned again, found every angle I could to examine the turn of my calf in their stockings. What a crime it was to hide such geometry beneath layers of skirts!
I was so transported by the sight of my gilded lower half that I had forgotten that I was bare chested. It was astonishing how natural it felt, and I supposed that it must be due to the breeches. How mercurial our sex must be if a pair of trousers could make me forget I was not born a man! I paused, the dream slightly fading from my mind: I had not planned beyond this point. Perhaps I should have put an end to it at this point. I had wanted to know the feeling of breeches, and I had achieved that aim. Yet, like Eve eating of the fruit of the tree of Knowledge, I felt that I could not turn back. I was drawn, inexorably, on.
My bosom was slight but not completely flat by any means. I found a solution by pulling on my jumps again and lacing them as tightly across my chest as the material would allow, somewhat squashing those inconvenient hillocks and flattening them into a shape that felt more manageable. The design of the shirt helped somewhat with this issue as the ruffles on the front seemed to disguise the curve of my chest well enough, and I was beginning to work on the row of buttons down the front when a sudden sound froze me in place.
At the beginning of my exploration through the trunk I had been careful to listen for any noises in the corridor outside– to make sure that I would not be discovered. Unfortunately at some point I must have forgotten to maintain my vigil because the door swung open and a man walked inside. For a moment he seemed as shocked as I was, and we just gazed at each other in silence. I felt as though I saw the exact moment his confused expression shifted as he recognised my face. Then, he closed the door behind him, and my heart felt like it was beating out of my chest. There I was, dressed in a man’s breeches and shirt, which I feared may be punishable by law if they chose to take it further, or at the very least would bring me ridicule and bring shame to my parents. I had no notion of what to say to defend myself.
My one hope was based on the fact that the man in front of me was not Flinn, the man whose clothing I had purloined, but his friend Crosby. Perhaps I had some small chance of convincing him to keep quiet.
“Why, Ned, I was not expecting to see you here,” he said smoothly, eyes glittering with something I could not interpret.
I felt as though I was gaping like a trout, the matter of my brains unable to understand. Slowly, a fragment of memory filtered through, and I dimly recalled hearing Crosby call Flinn ‘Ned’ before now. I was, I assumed, being offered a moment of grace. Perhaps this was his way of telling me he would pretend not to have ever seen me here.
“Ah– I am back for just a moment. I will go–”
“I see you’re making sure your best suit still fits,” his eyes drifted down my front, where I was only halfway through the buttons.
“It isn’t important. I will put everything back.” I said uncertainly, trying to play along with his game but unsure exactly what he was suggesting.
“Aye, of course, but we need to make sure that the rest is still in order.”
“I– the rest of the clothing?”
“It will be quicker if I help. Here, I always find it’s easier to do for somebody else.”
He stepped closer, and I could smell the lingering bitter scent of tobacco on his collar. Mr Crosby was larger than me in almost every way: taller, broader, more solid and substantial, but his fingers were gentle as he began to work on threading each small mother of pearl button through its corresponding slit. I watched his hands at work, feeling as though if I looked into his face I would find it harder to remain silent and stoic.
“This is the kind of shirt that was made for a gentleman to wear and for a gentleman’s gentleman to dress him in,” he told me, straightening the pleats at the points of my shoulders.
With an elegant gesture, he motioned for me to tuck my shirt tails into my breeches as he turned to the trunk to fetch something or other. I hurriedly did so, clumsily forcing the material down around the back and the front, my hands pushing down to smooth it flat. Crosby eyed me critically, an eyebrow raised as he lightly tugged a few inches of fabric back out, arranging and draping it so that the shirt hung more loosely over the waistband.
One of the items he had brought out was a long thin ribbon of dusty rose velvet. He lifted the stiff corners of my shirt collar and wound it around my neck, tying it in a bow across my throat. I swallowed as he arranged it thus, wondering what would happen if he decided to pull tighter: which would give way first between the ribbon and my larynx? I reasoned that the material seemed delicate enough to be a poor material for garrotting, and that I would at least have an opportunity to scream. Yet whatever this man’s motivation was, it did not seem as though he wished me any physical harm.
“Your cuffs, sir,” he said, truly seeming to have settled into his role as my valet, and once again I acquiesced, feeling that it was best to be agreeable for the time being.
He installed a pair of cufflinks onto my sleeves, and despite my anxiety over my position I could not help from marvelling at their design: each of the four matching cabochons glittered brightly and I thought at first that each was a polished gem until I recognised four perfect scarab beetles set in what I could only presume to be solid gold. How much would something like this cost? Once again I wondered who these men were, since clearly they were both involved. It occurred to me that perhaps I had some level of leverage here: I could threaten to reveal them both as thieves or confidence tricksters if I needed to.
I kept my chin upturned, my expression one which I hoped showed no fear or uncertainty as Crosby assisted me in threading my arms through the waistcoat and fastened each button down the front.
“The coat should be left open so that the rest of the clothes can be seen,” he told me, holding it out so that I could shrug each arm into it, feeling it settle onto my shoulders as though it was made for me.
In the looking glass I could see a portion of my body, enough of the middle section to see how the clothes were filled out by me, and yet I didn’t see a woman playing at dressing up as a boy for a masque. Perhaps it helped that my face could not be seen in the frame, but all I could see was the gentleman we had been playing at pretending I was. The exquisite coat looked even more attractive hanging from my arms than it had hanging flat in my hands. I found myself shifting in my stockinged feet to allow it to swish from side to side, to see how the gold thread glittered in the sunlight.
Crosby was watching me with an odd expression I could not interpret. I felt, suddenly, that my awe and joy at how well I looked in male livery was not only palpable but being judged and tested.
“Well, are we finished?” I asked with as much dignity in my voice as I could summon.
“Ah, have you forgotten? We still need to arrange your hair in its proper style, to appear a la mode.”
I had in fact forgotten that I was still wearing my plain cloth cap to cover my hair but it had not occurred to me at any point that the costume would include the hair. I allowed myself to be steered to sit on the stool in front of the dressing table, where I could see my full face in the mirror. To my eye I looked very strange, a high pink in my cheek that suggested I would not need any rouge. It was truly odd to see my head, as it seemed, pasted onto a man’s body.
Carefully, Crosby removed the covering from my hair. His own hair was clubbed at the nape of his neck and fastened with a black ribbon but I felt that such a style would not suit the extravagant suit I was wearing. True enough, a lacquered wig box was set down on the table to my side. I had never appreciated the intimacy that must exist between a servant and his lord until my faux valet began to run his fingers through my loose hair, brushing it back from my forehead and smoothing it with both hands. My scalp tingled pleasantly as fingertips brushed firmly over the skin, scraping handfuls of curls into place and securing them with pins. He seemed to know precisely what he was doing, and I wondered again about his history. Was this from helping Flinn, or did he wear wigs himself on occasion?
When he was satisfied with my hair being appropriately tidied away, the box was opened and the wig was taken out. It was white, and positively the tallest one I’d ever seen. It had tight curls by the side of the face in the cadogan style and lovelocks cascaded down from the back. It was truly in the style of the macaroni, a kind of fop I had only heard about as a mincing creature of no gender and no moral standing, but as it was placed on my head I felt as though I was a monarch being crowned with all the glory of the universe. My natural hair disappeared, tucked neatly underneath, and it took mere seconds for my mind to accept the swoop of ivory white as part of my appearance.
I watched in the mirror with rapt attention as the show continued for my own entertainment: Crosby covered my shoulders with a protective cloth while he applied a little powder to my temples, blending the edges of the wig to my skin. A different white powder was added to my skin, increasing the pretence of a pale complexion like an upper class creature unused to days in the sunlight would be more likely to have. With a great deal of art, some dark stuff was added to my eyebrows to shape them into black crescent moons, and an artificial blush used to restore my pink cheeks which had just been covered. At last my face was completed by painting my lips in the very centre to produce a delicate rosebud pout. To keep my face still while he created this masterpiece he held me firmly by the jaw, his own face very close to mine so that I could feel the soft exhalations from his nostrils on my cheek. I resisted the urge to close my eyes, resolute with the need to seem bold and unintimidated, instead watching the way his own eyes flicked over the curve of my mouth, his own lips parted in concentration.
As I’ve said, Crosby had seemed like the kind of man I knew, the ordinary earthy type who lived in the village I grew up in, or one of the many similar hamlets that dotted the countryside. He could have been the son of a miller, or weaver. I couldn’t place his accent exactly, but he sounded like he came from nearby, his way of speaking familiar and reassuring. As we continued our little play, his voice had changed, so subtly that I hadn’t noticed at first, but now he sounded as though he could pass as the valet he was pretending to be. Who were these men, either of them? Yet what surprised me even more was how naturally I found myself doing the same: I was playing the part of fop, so a fop I must be, and my rough consonants were clipped and plummy, subconsciously taking on the features of the occasional richer guest we had in the inn.
I assumed we now must have finished my costume, but there seemed to be yet more touches. My companion considered and then carefully selected a porcelain bottle and, using intimate brushes with his fingertips, dabbed scent onto my throat and behind my ears, which gave me the aroma of geraniums. Then he displayed a small silver box in the palm of his hand, showing me that it was full of snuff, and slipped his hand beneath the lapel of my coat to slide it into a pocket. Apparently every detail was important. Finally, he bid me turn around on my stool, turning his back to me for a moment to do something I could not see. He then presented a pair of pretty buckled shoes with a small heel, and after I pointed my toes in his direction, slid them onto my feet one by one. I realised that he had used some additional stockings or other fabric to stuff the square toes of the shoe, recognising that they might be too large for me. He had correctly gauged my fit, and although I would be unable to walk as comfortably as I could in my own clogs or rough leather boots, they were not loose.
He stood back, and I got to my feet, disguising a momentary wobble as best as I could. The added height to the shoes meant that I was a little closer to being able to look him in the face, and I found that being fully dressed had given me an added authority. Perhaps I had borrowed the spirit of whoever had owned this suit before Flinn and Crosby had acquired it.
“Does my lord approve?” he asked me, indicating the looking glass once more, and giving me more space so that I could move about and admire my form.
Even having been present for this entire process and witnessing a great deal of it coming together in the mirror, I would not have known myself. My heart fluttered as I watched my reflection turn: not merely a collection of fine clothes and a magnificent wig but a beautiful man. It felt like alchemy, or the product of some forbidden rite or witch’s bargain. Under the hands of a mysterious stranger I had been reformed like clay, created anew, fashioned from cloth and cosmetics and been reborn. I found that I wanted to beg him to allow me to remain this way, to hide me here so that I never had to return to my old existence, my old self who I couldn’t bear to think about just now.
“Yes,” I said breathlessly, looking him full in the face, and in my heels I barely had to stand on my tiptoes to kiss him on the cheek, leaving a smudge of lipstick behind.
A flash of surprise crossed his face for just a moment before he turned his head to kiss my other cheek in answer. I feel there was a moment, just about there, where polite gratitude tipped over into something else, and I possibly could have stopped it if I had been aware of what was happening. But I didn’t. Not only did I not stop it, but I threw myself forwards with wild abandon, throwing an arm around his shoulder and pressing myself closer to him, moving my mouth against the slight grainy stubble on his jaw, dragging up to brush lip against lip. I had never had a conscious thought of wanting to kiss him, but it was difficult enough to hold any thought whatsoever in the tumult of my brain, so confused that I had no idea what to feel or think other than to follow the instincts of my body.
His hands rested on my hips with a proprietary attitude while I greedily took my fill of kisses. I was not inexperienced in the art of love but there is a certain manner of behaviour expected from a woman to allow the man to lead, as though in a dance, which I have always found ridiculous. Certainly sometimes I may prefer to lie and allow myself to be explored like a lush wilderness, but perhaps on occasion I would like to be the explorer. Now, my role allowed me to act as I pleased.
Crosby’s fingers had moved between us to the buttons of my waistcoat but I batted them pettishly away.
“I would like to keep wearing this,” I explained, to clarify that I had no objection to him touching me.
“Remember you only have one suit of this quality, Ned– you wouldn’t want us to sully it,” he warned softly, peeling back one layer of our pretence, his posh valet voice sliding smoothly back into the way of speaking I had more familiarity with.
That was right: we were playing with layers upon layers. I was pretending to be Edward Flinn who was pretending to be some highborn popinjay. I appreciated the distance from my own identity, but I wondered how much truth there was in this pantomime. Did Flinn and Crosby ever touch each other like we were now, my hands sliding beneath the other man’s shirt and feeling the soft fur of his stomach? Did they kiss? Did they fuck? The idea of it sent a pleasurable shiver through my core, as well as a hot spike of jealousy. I did not want to be playing a part. I wanted to be fucked like a man fucked a man.
“You had better not make a mess, then,” I answered, fixing him with a saucy look as I unbuttoned the breeches and let them fall, stepping out of them and keeping on the stockings and even the shoes.
I was aware of how his gaze followed me intently as I moved to the bed, my shirt falling to mid-thigh so tastefully disguising the region between my legs, the tail of my coat likewise covering my plump backside. I knelt on the counterpane, positioning myself on all fours in the posture, so I believed, of the sodomite. I was only left waiting for a moment before my playmate was upon me, eager hands flipping the coat up past my waist and pushing all the clothing up out of the way. Both hands traced to my thighs, easing them apart roughly, and I felt the exquisite sensation of soft lips and a hot wet tongue pressing against my cunt from behind. I gasped with delight, needing to make an effort to stay upright.
His mouth continued to work at deeply kissing my molten centre but his hands disappeared from my legs. I glanced quickly over my shoulder to see him unbuttoning his trousers, just enough to free his hard prick which curved up towards his stomach. I found myself pleased that he was also keeping the majority of his clothes on: these trappings of masculinity. He shifted up, taking his mouth from my cunt and I leaned forwards slightly to grip the brass bedstead in anticipation.
A strange worry crossed my mind: as I have made clear, I was hoping to be fucked as men fucked each other. I was under the impression, perhaps a naive and simplistic one, that this must be forceful and powerful; I feared suddenly that he might consider this a bridge too far in our play, and would automatically default to using me tenderly, handling me with kid gloves, gentle and slow. I felt as though I would simply die if that was the case. It really felt as though he should have been able to intuit what I needed when he had done so up until now.
My lack of trust was misplaced. I needn’t have worried. With one firm hand on each of my hips, not even needing a guiding hand to aim, he drove his hips forwards and allowed my aching body to swallow him to the hilt. I dropped my head down to muffle my involuntary groans in the pillow, biting down as my cunt was stretched open around him. He didn’t allow me a moment to adjust, pulling back and driving home once more, his heavy bollocks slapping filthily against my skin, and I heard a desperate whine dragged from my throat that I’d never heard myself make before.
“Good boy,” he rasped, and I was delighted both by the praise and by the shake in his voice which suggested that I was having at least some portion of the impact on him that he was having on me.
He had done a very good job securing my wig, which stayed in place even while my head swung loosely on my shoulders and beat desperately into the bed, although I was certainly leaving a smear of powder which I would later regret as the one who would have to wash these sheets. One of his hands snaked around my stomach, cupping my mound firmly to use as leverage for his thrusts and also to rub insistently at the hardened nub of flesh I had there, swollen from arousal, and my fists tightened fiercely around the metal rails. No man I had bedded previously had shown much interest in that area, seeming to assume that I would derive all pleasure from giving myself to him, and I usually did not trust them enough to demonstrate how I would stimulate myself when alone.
I almost felt as though I could bear it no more, delirious with the lust that I felt increasingly unable to contain, my knuckles white as I gripped the bed and my smeared lipstick almost fully rubbed off as I bit harder on the pillow, when Crosby pulled out of me and I found myself swearing and whimpering in a rush of confused desperation. Yet almost immediately he stuffed several fingers– at least two, perhaps three– in my poor vacant cunt, and I felt an immediate pressure in the hole just above.
“Oh yes, yes!” I all but sobbed as he used the plentiful wetness coating his shaft to aid its entrance.
“A proper little catamite,” he snarled, thrusting his way deeper, as I lifted my hips higher to aid him in buggering me fully.
His fingers curved up inside me and I wondered if he could feel his own prick through the meagre flesh barrier. I had never felt more full, more blissfully used. I was being taken apart, fucked to pieces, and I urged it on, demanding my own complete obliteration. The slight pain was tolerable, I dare say even enjoyable, and I feel my pleasure was increased by the knowledge that I was participating in a sin. Our skin smacked together, our hips moved in tandem, and I felt as though I finally understood the appeal of carnal pleasure which I had only had the meagrest of glimpses at before now.
I cannot stress enough that most men had shown very little interest in my pleasure and my only climaxes until now had been at my own hand. I had not necessarily expected anything different from this interaction, assuming that this was simply how it must always be. Instead I was brought to a shuddering, quivering and moaning peak, unable to see anything as my vision rolled into an obsidian nothing, my ears ringing and my body seemingly seized as though I was a lightning rod struck again and again. I slumped down, pressing my face hard into the pillow and practically suffocating myself to stay as quiet as I could, while Crosby gripped me harder to stop my knees from giving way, not pausing even for a moment as he fucked me faster, groaning deliciously from above me, until he too collapsed forwards with a final gasp and I could feel him pulse inside me, thrusting spurts of meltingly hot seed into my insides. I could do nothing but slowly sink further onto the bed with a satisfied groan.
After the briefest moment where we lay fused together he disengaged with a soft sigh, taking his handkerchief from his pocket and dipping it into the wash basin to help me clean up. In silence we stripped the clothes from my still-trembling body: I was so used to the feeling of the suit that it felt like he was peeling off my skin as he removed my coat, my waistcoat, my shirt, neatly folding each one to replace in the trunk as though nothing had happened. I took off the wig myself, getting up with shaking legs to wash the remnants of makeup from my face. I couldn’t bring myself to replace the rest of my own clothes just yet, taking off my jumps in preparation to put the shift back on underneath them and lounging on the bed, fully nude.
It may sound strange, but in this state, after just having taken off the clothes of a man, I did not feel as though I had returned to womanhood. Perhaps I would feel differently once I had put on my gown and cap, or once somebody had called me by my Christian name rather than that of a man. Perhaps that was why I was delaying that process for as long as possible. In that moment however I felt like nothing other than myself, and I mused, basking in the warm triumphant afterglow, that I had the power to form that self however I desired.
