The Chelmsford Academy

“After mommy and daddy caught me with Uncle Charlie the shit hit the fan, as the common folk are want to say. Even though daddy gave Charlie a thrashing and drove him into bankruptcy, his motive wasn’t revenge for me. He did it because Uncle Charlie had broken daddy’s trust. I could tell by the look on daddy’s face that he was horrified when he saw what he thought was Belinda, his pride and joy, being rogered by Charlie. When he realised it was me, his look turned to disgust,” Julia Wallace began her third therapy session.

Julia had arrived wearing a red Dior skirt-suit, nylons and Jimmy Choo heels. Her makeup was impeccable as usual but the bitchy side of Susan Bradshaw couldn’t help thinking of Julia as an entitled matron. Susan was also wearing a designer skirt-suit. When she had bought it three days earlier she had tried to convince herself that the extravagance was not because she envied Julia Wallace but subconsciously she was not convinced.

Julia had settled into the chaise lounge, kicked off her heels and continued her confessions despite Susan wanting to explore the physiological consequences of Julia’s trauma and begin the healing process.

“At this stage I just want to get it all off my chest. I need to share my memories with someone I can trust. Up until recently I thought that I had been sent to boarding school just because daddy had found me crossdressed drinking his liquor. I had suppressed the memories of the sexual encounters with Uncle Charlie deep inside me and now I need to tell you the rest. As I told you during my first visit I find it cathartic,” Julia had insisted.

Susan had allowed Julia to continue. It might be best to hear everything Julia had to say before she began to fully psychoanalyse the consequences.

“I didn’t tell mommy and daddy that Belinda had helped me with my transition from Julian to Julia. I loved my sister too much for her to be dragged into the sordid mess. She was at Oxford living-in at Lady Margaret Hall and blissfully unaware about what was going on at home,” Julia sighed.

“My father made me gather up all of my feminine attire and my makeup and forced me to burn it in the furnace. He told that I was never to speak about what had happened with Uncle Charlie and was not interested in my side of the story. He was disgusted with me and gave me the option of being thrown out of the house without a penny or going to boarding school where ‘they would make a man of me’. What else could I do?” Julia posed the rhetorical question.

“The Chelmsford Academy for Young Men was one of the last all-male institutions where strict discipline was enforced. The prefects maintained order outside of the classroom and the schoolmasters' authority was almost limitless. I was given a haircut, short-back-and sides of course, uniforms were purchased and I was packed off to the Academy and daddy told that if I didn’t graduate with honours, I would be disowned,” Julia recalled wistfully.

“You probably don’t realise what boarding schools were like back then, men and boys living on top of each other in a testosterone-fuelled melange. The practice of juniors fagging for the seniors had only just ceased when I got there but there were cliques and alliances within the Houses and if you were on the outer you were ostracised. Students only went home for the holidays and the school was a hotbed of suppressed sexual frustration,” Julia recalled.

“It was an open secret that some boys gave each other an ‘Eton rub’ now and then to let off steam and a few took it further,” Julia commented.

“My roommate was Byron Rumsfeld. He was the same age as me, a short chubby chap who the bullies called ‘Piggy’. Being effete and not particularly athletic we were both the subject of bullying which in those days was not discouraged. Although I excelled academically I did not do well in manly pursuits. Sport was compulsory but there was no badminton or tennis. We had to play at least one team sport, either Rugby, football or field hockey in the winter and cricket or softball in the summer. Boxing was a year round event. I wasn’t much good at any of them although I did well at cross-country running,” Julia recalled.

“Piggy and I were hopeless at rugby and spent our time on the bench or running out oranges and water at half time. Every now and then Timothy Valentine, the team captain, would put us on the field so the other boys could watch us get pummelled in the rucks. The one saving grace was that Chelmsford Academy did have an arts department and that was where I took my elective subjects.”

“Shakespeare was what the school’s theatre company mostly performed and I found I had a natural inclination to act. I shouldn’t have been surprised. Hadn't I been acting when I presented as Julia back in London? A new Master joined the staff who was inclined to produce a modern farce and all of us in the theatre class were relived and elated to be performing something more up to date,” Julia gave a rare smile.

“It was an absurd pasquinade involving two married couples. Both wives have been unfaithful with the other’s husband but each spouse had kept the affair secret from their partner. There was lots of innuendo and double entendres when the couple reunited for a dinner party at one of the couple’s houses, having not seen each other for many years. Many of the Masters did not want the play to be performed but Mister Dillingham, the new arts Master, finally got approval to do something more light-hearted and comical.”

“‘Why don’t we audition for the female leads?’ Byron asked me. ‘They are hilarious roles and we can camp it up,’ Piggy was enthusiastic. He thought that playing the fool on stage might make us more popular with the cliques. Of course I was dying to take on the role of Penelope, the vicious-tongued shrew, not just because it was a meaty role but because I could legitimately crossdress. In my dreams I was still Julia, although I hadn't been able to present as her for nearly a year,” Julia said a little bitterly.

“I was a shoe-in of course. I had the mannerisms, the voice and the aesthetic down pat, in fact I had to be careful not be overly feminine otherwise I might give my secret away. Mister Dillingham gave the other female role to Byron mainly because his short tubby appearance and bumbling awkwardness was the perfect visual foil to my tall, slim appearance, elegant grace and charm. He cast two handsome boys to play our husbands,” Julia smiled again as she recalled the memory.

“So you were able to fulfil your desire to present as feminine by playing a character in a play,” Susan scribbled away in her notebook.

Julia looked a little annoyed that Susan had interrupted her train of thought but she took a sip of water and continued.

“We rehearsed without costumes while the other art and theatre students worked on set design, props and lighting. It felt quite peculiar playing a female role whilst dressed in my school uniform. When we were ready for dress rehearsals I was finally able to fulfil my secret ambition.”

“The costume department had done an excellent job. The play was set in the 1950s and they had taken our measurements and had acquired suitable costumes for myself and Byron. I was provided with a red sleeveless spaghetti strap satin evening gown, with a split in one side as suited my character. Byron was given a vintage cocktail party swing dress. It was emerald-green with black polka dots made from ruched mesh with tulle details. Matching high heels were provided and to my delight the costume designer insisted that we wear vintage lingerie and hosiery for authenticity,” Julia gave a wry smile.

“The clothes had been found at Oxfam by Mister Dillingham, the lingerie and hosiery purchased at Debenhams. Two dinner suits had been acquired for the male leads and the costumers worked hard tailoring them to fit us. I was to wear a glossy raven blunt-cut bob in keeping with Penelope’s sharp-tongued shew and Byron was given a blonde wig that was coiffed in a mixture of soft, voluminous curls and waves worn in a side part, with the curls cascaded down the face and shoulder. Think Marilyn Munroe. Needless to say I was jealous of her hair but I was happy just to be able to dress femme.”

“The makeup department, which consisted of one chap whose skills were limited to applying stage makeup to Shakespearian characters, didn’t have a clue but I let him make up Byron and I. Mister Dillingham was not impressed with his efforts.”

“‘These women need to look sexy and seductive, alluring, mature and sophisticated. Their makeup needs be theatrical but also realistic,’ Mister Dillingham said. I could have kissed him for using the word ‘women’ to describe us. ‘I watched my sister do her makeup. She even made me up a few times,’ I offered, steering close to dangerous shores by admitting so. But Mister Dillingham gave me a free rein to effect Penelope and Betty’s makeup and I was pleased with the results,” Julia confessed.

“I was of course delighted that I was finally able to put on makeup again after such a long recess. Byron was impressed too and when he looked in the mirror and saw his face feminised by the heavy makeup and the blonde wig I could tell he was pleased. Of course dressing for the first time in foundation garments, stockings, high heels and my evening gown was exhilarating. Now that I was wearing my blunt-cut bob wig and my makeup I felt like Julia had been resurrected.”

“The company was impressed with how I projected femininity and how well I took to the bitchy role. I coached Byron, whose character Betty was a dumb blonde, a foil for my wicked tongue, and she was very taken with her role. Late one night as we lay in our beds in the dark Byron asked me why I was so proficient and comfortable with makeup, why I hadn't stumbled like she did when we first wore high heels, how I was able to project femininity without coaching and I realised that I’d overplayed my hand. I confessed to Byron, who I only thought of as ‘Betty’ when she was dressed for her role, about my past and what had happened with Uncle Charlie.”

“‘That must have been awful!’ Byron whispered. ‘It was. But also it wasn’t. Uncle Charlie only ever treated me as a woman, even though I was under duress when he was doing those things to me. Yes it was degrading but it was also empowering,’ I whispered to him in the dark and we left it at that,” Julia sighed.

“We were allowed to invite family and friends to the Friday night performance but of course I didn’t invite anybody. If mommy and daddy knew that I was playing a female role in the play they would have had a fit. Daddy was not happy that I had taken theatre as an elective but I was top of my class in my academic subjects to he let it go,” Julia said wistfully.

“I remember our opening night like it was yesterday. It was the Thursday night before the premier performance, what we now call a ‘soft opening’ and only the students and staff attended. The play would run for a week and then we were to switch our endeavours to Othello,” Julia made a mew with her mouth.

“I remember cinching my garter belt around my waist, the suspenders tickling my thighs, sliding the fifteen denier fully-fashioned stockings up my legs followed by my tight satin knickers. A padded brassiere gave me shape and as I sat in front of the mirror and did my makeup, heavy, theatrical but sexy, then positioned my wig on my head and brushed it out, I felt contented. I already looked like Julia but when I slipped into the satin sheath gown and put on my high heels and the costume jewellery, I looked stunning. I might be Penelope Watson for the play but inside I was Julia,” Julia sighed contently.

“Byron looked nearly as stunning presenting as Betty, a bubbly buxom blonde. I helped Betty with her makeup before she dressed. She had become quite adept at presenting feminine and had taken on the role as comic counterpart to my snarky bitch to heart. Even then I thought that Byron liked dressing up as Betty a little more than he admitted but I didn’t realise Betty’s perfidiousness until later,” Julia gave a wry smile.

“Then we were on stage and performing and I immersed myself in my role as did Betty. The two young men playing our husbands also performed their roles brilliantly. There were a couple of kissing scenes in the original version of the play but for modesty’s sake they had been rewritten as chaste pecks. Neither Betty nor I felt any licentiousness from or for the two male leads. We both knew that they were closet queers and had no interest in us ‘ladies’.”

“After the performance I stood at the edge of the stage with my three fellow actors, all holding hands. The two ‘husbands’ bowed and Betty and Penelope curtseyed, which effected more applause and laughter from the audience.”

“Then I saw them… three prefects sitting in the front row. They were seniors in their early twenties undertaking their final year at the college,” Julia’s eyes glazed over a little.

“I saw the look of hunger in their eyes. It was the same look that I had seen in Uncle Charlie’s eyes when he stood in the lounge room doorway staring at me that first time. They were men, devoid of female company, not averse to using their strength and influence to take gratification from weaker lads,” there was a creak in Julia’s voice as she spoke.

“These were the same three young men who had bullied Byron and I incessantly and who accused us of being lavender, which was the college euphemism for effeminate homosexuals. Was I afraid? Yes. But I was also smug and vain. I knew that I looked pretty and seductive standing on that stage under the spotlight. I was foolish and would pay for my vanity,” Julia said coolly.

“The Chelmsford Academy had a large function room and each House had a small bar. The function room would be used for the Friday night post-performance reception but because not all of the students had attended and some of the faculty had boycotted the play, one of the smaller House bars was used for the after party on completion of our performance. The four principals attended in costume, I touched up Betty’s makeup and my own before we attended,” Julia continued.

“The Headmaster gave the briefest of speeches and said that he was looking forward to the company’s forthcoming production of Othello, openly conveying his dislike of the farce. Mister Dillingham however gave a flowery speech, praising everyone in the academy’s theatre production team and especially his four principals. I enjoyed pretending to be Penelope Watson whilst secretly celebrating the return of Julia Wallace and I noticed that Betty seemed to be enjoying attention that she seldom achieved as ‘Piggy’.”

“There was some light-hearted horseplay, what our American cousins refer to as ‘grab-assing’ and I probably drank more than I ought to because I was on a high. Later in the evening I saw Betty surrounded by the three prefects, having what appeared to be a heated discussion, but when I approached the three bullies quickly disassembled and left the party. I asked Betty about the confrontation but she said it was nothing, just the prefects giving her cheek.”

“The party broke up and Betty and I made our way back to our dorm. We would return our costumes to the theatre the next day. Betty opened the door to our dorm room and let me enter ahead of her. She entered right behind me and I heard her lock the door. I watched in amazement as she tossed the key across the room. It was caught by Tim Valentine, one of the prefects. He was sitting in an armchair waiting for us. His two chums were standing nearby. They all had evil grins on their faces and openly ogled Betty and I,” Julia swallowed and took a drink of water.

“‘I’m sorry Julia, they threatened me. I’ve been their plaything for so long now that I just couldn’t say no,’ Betty was close to tears but in that moment I hated her,” Julia’s eyes were icy.

“‘Yes, Piggy has quite a good mouth on him and that fat arse is very comfortable but I much prefer her as Betty. And you Penelope, or should I say Julia, are absolutely stunning,’ Tim Valentine sniggered. I was no fool. I knew what they wanted. I’d heard rumours that some of the prefects bullied some of the lower classmen into providing sexual favours,” Julia knitted her brows knowingly.

“‘You chaps can play with Betty, I’m keeping Julia all to myself for now,’ Tim waved a hand at his classmates dismissively and strode over to me. I knew what he wanted of course. The same thing Uncle Charlie and his friend had wanted. The only question for me was would I get away with giving him a little ‘slap and tickle’ or was I in for a buggering? Calling for help would be a waste of time,” Julia said a little pragmatically.

“‘How do you know about Julia?’ I asked defiantly but the answer was obvious. I had been betrayed by my roommate. ‘I know all about Julia and your Uncle Charlie because Betty told me. All I want is the same thing. It’s nothing you haven’t done before,’ Tim Valentine stood inches away from me with a smarmy grin on his face,” Julia took another sip of water and proceeded.

“‘You are quite stunning you know Julia. Possibly better looking than any of my girlfriends in London and you definitely have better legs,” Tim slipped his hand inside the slit of my gown and stroked my leg. His fingers fluttered lightly on my stockings and little wavelets of pleasure radiated from where he touched me despite my attempts suppress them,” Julia admitted.

“Tim was a handsome lad and when he kissed me I could smell his aftershave. I could feel his muscled torso pressing against me, his cock was tenting his trousers. I expected him to be rough and insistent but his lips were soft and his tongue slipped easily into my mouth and he held me close, putting his arms around me. Of course my natural inclination was to fight him off but what would that achieve? He was bigger than me and he had his two housemates with him. The door was locked and he had the key, there was no escape,” Julia sighed.

“I think it was the author Lawrence Block who wrote in his novel The Thief Who Couldn’t Sleep: 'when rape is inevitable, lie back and enjoy it.’ Of course it is often quoted out of context but the axiom seemed appropriate at the time,” Julia sniffed as if what she had said was a trifle.

“I’m sorry I have to stop you there Julia. Are you really advocating that women should just submit to sexual assault and that they should somehow savour the experience?” Susan Bradshaw sounded outraged.

“Of course not you silly woman. Now you are taking me out of context. Put yourself in my position. Back then I was a young man who liked to… no that’s not right… was compelled to crossdress. As I have said many times, I felt most comfortable, normal if you will, when I presented as Julia. I was still battling with my gender identity and sexuality. I was locked in a room with three ardent young men and another crossdresser,” Julia retorted.

“Tim Valentine was a handsome young man and he was kissing me and telling me how beautiful I was. He was validating my femininity and if the price I had to pay to receive that validation was to submit to his desires I was willing to pay it. Now let me proceed,” Julia said indignantly.

Susan just nodded but it was obvious that she disagreed with Julia but it was not Susan’s place to judge; her job was to support Julia, not to take her inventory.

Julia proceeded with her confession.

“Tim was kissing me and holding me tight. I didn’t fight him but I didn’t encourage him either. I was once again confused. Men found me attractive, of that I was certain, but they only saw me as an object of desire. I could sense Tim’s ardour, his lasciviousness, his need. My thoughts vacillated between contempt and felicitation. Tim despised Julian and bullied him incessantly but he desired and coveted Julia,” Julia reflected.

“So I immersed myself in the pneuma of Julia as others saw her: Uncle Charlie, the stranger, and now Tim Valentine. They all deemed me a strumpet, a concubine; theirs to ravish and despoil. So I took Lawrence Block’s adage literally and I surrendered. I returned Tim Valentine’s kisses. I moulded my body to his. I sought out his appendage and stroked it through his trousers,” Julia sighed.

“He gasped into my mouth as I fondled his bloated penis, my tongue fluttering in his mouth, his hand stroking my thighs. My cock began to engorge and sprang forward, tenting my knickers. My testicles descended from where I had tucked them away. Tim’s fingers brushed the front of my knickers and I shuddered with delight but he quickly removed his hand from my pubis and instead squeezed my buttocks.”

“‘I don’t want to touch it,’ he whispered in my ear. ‘But you want me to touch yours,’ I nipped his earlobe and unzipped his fly. ‘Yes, oh god yes!’ he gasped as I locked my fingers around his swollen cock. I stroked it and rubbed it on my stocking and felt Tim shudder. I could feel the warm slippery milt of his pre-ejaculate on my fingers and soaking into my stocking when I put his cock between my thighs and let him dry-hump me,” Julia swallowed as she recalled the events of the evening.

“‘I don’t want to cum yet,’ he groaned into my ear.”

“I knew then that I could make him cum right there and then. Most likely once he had climaxed he would push me away and I would be done with him, at least for now. It would be a small victory for me. But something about his yearning for me, his desire and his need felt flattering and gave me power and control.”

“It surprised me as much as it did him when I suddenly dropped to my knees and took his engorged manhood into my mouth. I don’t know what came over me but I had suddenly become the slattern that I’m sure Tim and his prefects imagined I was. Tim had his back to the wall, his eyes screwed tightly closed, his mouth open in a continual moan, his hands resting lightly on my head, guiding my lips up and down his cock. I lashed my tongue on the head of his penis and swallowed his salty-sweet precum as his cock juddered in my mouth.”

“I could sense that he was nearly at extremis and I wanted dearly to free my cock from my knickers and orgasm right along with him but I resisted the temptation. Tim suddenly pushed my face away from his groin and he dragged me to my feet and began to kiss me again. I rubbed against him, returning his kisses. When I reached for his erection he batted my hand away. ‘Not yet. I don’t want to cum yet,’ he gasped,” Julia took a beat and then continued.

Susan could feel the dampness in her knickers as Julia told her tale. Despite her sexuality she had dallied with boys when she was younger and she could imagine what it was like for Julia being willingly molested by the handsome young Tim Valentine.

“He led me to my bed and I lay down on it. On the bed across the room Betty was kneeling on her hands and knees being buggered by one of the prefects while the other one stood at the end of the bed feeding his cock into her willing mouth. By the look on her face she seemed to be enjoying every second of it as she pushed back against the boy buggering her, her red lipsticked lips slathered at the penis in her face,” Julia’s description was graphic.

“The prefects had come prepared and Tim snatched up the jar of Vaseline that stood on the table between the bunks. He lifted my legs and put my ankles on his shoulders, pausing to kiss my nylon-sheathed calves. He had removed his trousers and his shoes and he knelt between my legs with his angry member standing proud, a rivulet of silvery precum hanging from the eye,” Julia closed her eyes as she recalled the incident.

“He eased aside the gusset of my knickers and anointed my sphincter with a good dollop of Vaseline. He put the lubricant back on the table and stared into my eyes. ‘You really are beautiful,’ he whispered and lowered his face to mine and kissed me as his long corpulent phallus slid inside me,” Julia said wistfully.

“I should have protested. I should have screamed. I should have been in agony. But I wasn’t. I was in bliss. That long fleshy prong lit up the nerve endings around my tight sphincter, his glans pressed on my prostate. I wrapped my arms and legs around him and held Tim close while he fucked me. He barely moved his cock because he was scared that he would ejaculate too soon. I kissed him passionately and scissored my stocking-shrouded legs on his flanks and crossed my ankles behind his back as his cock filled my tight anus.”

“He returned my kisses and moaned into my mouth, then I felt his cock begin to bloat and pulsate as he filled me with his scalding issue. I came at the same time flooding my knickers with my slick, slippery spend, waves of pleasure radiating from my cock-filled anus. We lay in each other’s arms, locked together in a tight embrace as our orgasms peaked and then we basked in the afterglow,” Julia’s eyes were still closed but she was smiling.

“Fortunately I’d had the sense to ruck my gown up around my waist when Tim laid me on the bed because his semen began to dribble out of my anus, and when he retracted his deflating member from my sphincter a flood of spunk and a modicum of ejectamenta dribbled down between my legs. I quickly ripped the pillowcase off one of pillows and used it soak up the mess and wipe away the excess jism from the front of my knickers,” Julia gave a wry smile at the memory.

“I somehow got to my feet without staining my dress and did my best to look dignified. Tim was putting on his trousers and shoes whilst his fellow prefects waited for him. They had finished with Betty who was lying on her bed smoking a post-coital cigarette and looking smug. Tim came over to me looking a little embarrassed with a meek smile on his face. ‘See you tomorrow Julia. Come to my dorm after the show,’ he kissed me quickly on the lips and he and his acolytes left, closing the door softly behind them,” Julia opened her eyes and looked at Susan.

“I have used the word concubine many times during my confessions. In past times, a concubine was often a slave whose rights and obligations varied tremendously according to her master's whim. I became Timothy Valentine’s concubine for the remainder of his time at the Chelmsford Academy. Seniors had the luxury of single rooms and every evening I would transform into Julia and visit Tim in his room,” Julia confessed.

“How he treated me depended on his mood but he mostly treated me well. He even bought me lingerie and jewellery. I kept a small wardrobe in the dorm I shared with Byron who kept his own little stash of feminine paraphernalia and often presented as Betty and ‘entertained’ some of the prefects while I was attending to Tim.”

“I think Tim had genuine affection for me although of course he never displayed it outside the confines of his dorm. Depending on his whim I might be summarily bent over and fucked viciously and then sent away or he might take me into his bed and we would spend all night making love. I think he subconsciously loathed himself for having a deep affection for a transvestite just as I secretly loathed myself for falling in love with him,” Julia sighed.

“I now know that what I really felt was infatuation. I was obsessed with Tim. I felt euphoric when I was in his presence. As Justin I disliked him. He and his cronies continued to bully Byron and me because they had to maintain the sham. But when I presented as Julia and Tim held me close and kissed me and told me that I was beautiful and that he thought about me all the time, I forgave him. Never once did Tim touch my penis and he preferred it if he never saw it. I kept my knickers on during sex and often wore tights so I could keep it tucked away. He couldn’t bare it that I was really a boy dressed as girl but he couldn’t stop summoning me to his room,” Julia stopped talking and took a long drink of water.

“I think we should end it there. We have a lot to discuss next time we meet. This is the first time I have heard you use the word love and I think we need to explore your symbiotic relationship with Timothy Valentine a little further,” Susan said.

Susan made some final notes in her notebook while Julia put on her heels. She showed Julia to the door and then closed and locked it.

The waistband of Susan’s tights dug into her wrist when she lifted her skirt, put her hand inside her knickers and rubbed out a quick orgasm. After an earth-shattering climax she adjusted her underwear, smoothed out her skirt and told her receptionist to send in the next patient.

To be continued…