Chapter 2: Purging

Stephen Nielsen’s Apartment, New Brunswick, Newark – Fifteen Years Earlier

Craigslist turned out to be goldmine, full of men seeking to have sex with crossdressers. Under Tessa’s tutelage, Stephanie learned how to post an ad in the Casual Encounters section and how to vet replies.

“There are a lot of wierdos out there and although you can vet replies sent via email, it’s best to use your mobile phone and receive texts. You can pretty much figure out who is genuine and who is wasting your time. A lot of email responses will be from guys who are just picture-hunters, requesting compromising pics,” Tessa explained.

Stephen had purchased a cheap laptop and a pay-as-you-go burner phone on Tessa’s advice.

“Keep your real identity and your femme identity separate from each other. It’s safer and more discreet. Have you ever watched Ghostbusters? ‘Don’t cross the streams’. That’s pretty much a rule with us closet crossdressers. You can’t post a phone number in Craig’s and they have an algorithm that searches and removes ads that have phone numbers posted in them but it’s easy to beat,” Tessa helped Stephanie post her first ad in the T4M section under Casual Encounters.

Young attractive femme crossdresser hosting for NSA on evenings and weekends. D&D free genuine applicants twenty to fifty, no timewasters or picture collectors. Too Oh Won For Too Sux Ate Fife Fife Fife. See pics to see what is on offer.

This was Stephanie’s first ad and she attached some cheesecake shots to entice potential candidates.

Soon Stephanie was hosting men for sex most evenings and weekends and it became obsessive. She had a group of men whom she called her ‘regulars’. These were men whom she deemed compatible and were able to meet regularly at prearranged times. Most told her little about themselves but she soon realised that the majority were married ‘straight’ men seeking something spicy on the side.

Of course many of the responses Stephanie received were from timewasters but Tessa educated Stephanie as best she could how to sort the genuine trans admirers, as Tessa called them, from the bogus responses and those that looked a little shaky.

“The reality is, until the guy turns up at your door, you never know what you are dealing with,” Tessa explained the bleeding obvious.

The first couple of times that Stephanie hosted men in her apartment she had Tessa with her and they had posted an ad offering a threesome. Once Stephanie was confident that she knew what she was doing she began to host on her own. Tessa was tiring of Stephanie anyway. Terrance Bigalow was a married man who occasionally crossdressed as Tessa to engage in extramarital gay sex and she couldn’t keep up with Stephanie’s voracious appetites.

There were a few abject failures who after the first meet were not invited back but Stephanie felt secure because all of her transactions took place on her private laptop and ‘burner’ cellphone.

The problem was that Stephanie was taking over Stephen’s life. Stephen spent most of his free time as Stephanie and his grades began to suffer and he wasn’t socialising. Although it was only a two hour drive to New Rochelle, Stephen didn’t get home much and Astrid Nielsen became worried about her son. She had heard about his falling grades and she contacted the Dean who had administrative responsibility for her son and the news was worrying to say the least.

Astrid immediately thought drugs were the problem, although Stephen denied it. Astrid decided that drastic action was required to steer her son back on the straight and narrow path of academic achievement and appropriate social interaction. She would limit Stephen’s access to the family fortune and cease paying rent on his apartment and force him to reside in the on-campus student accommodation and reduce his spending allowance and tie the amount of money he received to his academic achievements.

Before she did any of these things an event occurred that changed Stephen Nielsen’s life drastically.

Although Stephanie had a bevy of admirers, mainly older married men, she still posted her ad in Craigslist looking for conquests. She adored the fact that some men found her irresistible and craved her company. It validated her femininity. She had also participated in group sex now and then when the mood took her. She was promiscuous, precocious and almost insatiable.

She received a response from a man named Oliver who claimed to be an experienced trans admirer who had a particular penchant for young crossdressers. He texted her and sent pictures to her email account. He was mid-thirties, handsome and seemed a perfect candidate. She arranged a meet with him and gave him the address of her apartment block but not the apartment number. As Tessa had taught her, the admirer did not get the apartment number until he was out front.

Stephanie was dressed in a sassy French maid’s costume she had bought at Party City. It featured a black satin dress with white lace trim and an attached white apron and a white lace headband and black velvet choker. She wore black transparent boy leg panties under it, black, fully-fashioned stockings and black high heels. She wore a blonde shoulder-length wig and her makeup was slutty. The costume had been specifically requested by the handsome man who had answered her ad and he had asked her if she was wearing it when he texted her requesting the apartment number.

When she opened the door there was no handsome mid-thirties man. Instead there was a fortyish, stout, muscular, big-bellied man with a boxer’s face and standing behind him was a skinny man with lank greasy hair around the same age and an obese man with a pockmarked face and permanent scowl.

“Hello princess,” Oliver pushed the door wide open before Stephanie could close it.

The three men crowded Stephanie inside and slammed the door behind them and locked it.

“Hey, this isn’t the deal!” Stephanie knew that her voice sounded high and whiney but she was scared.

“She’s hot Ollie, those pictures on the website didn’t do her justice,” said the greasy haired man who had already begun to undress.

“I’m going to fuck her brains out,” the obese man said stripping off his shirt to reveal pale white flesh that was also pockmarked.

“Come on guys. This isn’t what I was putting out there and you are definitely not the man in those pictures,” Stephanie said to Oliver who was ogling her openly.

“Hey, you advertised yourself as a tranny looking for a fuck, so look on the bright side. You’re getting three for one,” Oliver chuckled.

Stephanie tried to bolt for the door but Oliver caught her by the wrist and swung her around. She landed face to face with the skinny, greasy haired man who clutched her in a bear hug and tried to kiss her. He chased her lips with his mouth and his breath was terrible. He eventually clamped his lips on Stephanie’s and drove his tongue into her mouth while he frogmarched her into the bedroom. The others followed and closed the door.

The three men were naked and erect and Stephanie was terrified. She knew what was going to happen she just hoped that she wouldn’t be injured or worse. She had read about home invasions in the media and she silently prayed that all they wanted was sex.

“You go first Frankie, I want her to suck my cock,” Oliver said to greasy-hair and Stephanie paled.

“Frankie here is going to fuck you a little while you suck my cock and Jimmy is going to watch and take his turn next. If you fight us Jimmy is going to hurt you. If you scream or cry out, Jimmy is going to hurt you. If you try to bite or scratch, Jimmy is going to hurt you. Do you understand?” Oliver hissed holding Stephanie at arm’s length next to the bed.

Stephanie was too shocked and scared to say anything and she just hung there like a rag doll.

“Show her Jimmy,” Oliver said when Stephanie didn’t answer.

The punch to the midriff winded Stephanie and the pain was excruciating. Lucky for her it was a short, sharp jab and she recovered quickly.

“I understand,” Stephanie gasped for breath.

“Good. Now get on the bed,” Oliver pushed Stephanie onto the bed and he and Frankie pulled Stephanie to her knees.

“Check out that ass!” Frankie pulled the hem of Stephanie’s French maid’s costume all the way up, exposing her rounded buttocks sheathed in the black transparent panties.

Stephanie had to endure being forced to her knees on the bed while Frankie took up position behind her and Oliver scootched down in front of her, his big cock dangling inches from her face. Oliver put his hands on Stephanie’s head and guided her mouth onto his quivering organ. A rope of pre-ejaculate dribbled from the eye and Stephanie tasted the salty-sweetness of it as her lips circled Oliver’s bloated glans.

At the same time she felt her panties being eased aside and suddenly Frankie’s long but thankfully slender penis slipped inside her anus. She thanked god that she was pre-lubricated in anticipation of sex when Frankie dug his fingers into her hips and began to vigorously fuck her.

Oliver entwined his fingers in Stephanie’s hair and began to fuck her face. He fucked her mouth so viciously that her wig came off in his hands and Frankie, Jimmy and Oliver all laughed at Stephanie’s distress. Jimmy tossed the wig aside and Oliver twisted his fingers into Stephanie’s dirty-blonde hair and tugged, forcing her face back onto his engorged prong.

Stephanie knew that her only hope was to satisfy these men’s desires and hopefully she could escape unscathed or with as little damage as possible, her belly still ached from where Jimmy had punched her.

Frankie was fucking Stephanie with long slow strokes, enjoying the feel of her tight anus stretched around his steely rod whilst Oliver delighted in the feel of her lips gliding back and forth along his shaft while Stephanie’s tongue slathered at his glans, the tip of it ticking his fraenulum.

Stephanie was using every trick she knew to try to get these guys off so they would finish and leave. She looked up at Oliver with her frightened green eyes, her red lips distended around his turgid shaft whilst she fellated him, trying her best to induce sympathy but also to illicit his climax. She pushed back and gyrated her panty-clad buttocks into Frankie’s groin as his cock slid in and out of her rhythmically.

Stephanie felt almost disembodied. It was like she was in a trance, standing beside the bed, watching her doppelganger being ravished. Worse still she was becoming erect. Frankie’s slim banana-shaped phallus was the perfect shape and size to light up the pleasure receptors in her prostate, the base of his organ elicited sparklets of delight from her stretched sphincter. It didn’t help that Jimmy had his hand between her legs, stroking her erect organ through her gauzy panties.

It was a nightmare, come true. As much as Stephanie despised these dirty hooligans she couldn’t prevent her body responding to their ministrations. Frankie knew how to fuck and he was enjoying every second of defiling Stephanie’s tight, slick anus. He would push his cock all the way inside in her and jiggle his cock, stretching her sphincter, feeling the velvet sheath of her rectum clench and release his hard cock. He gazed at her plump white buttocks, sheathed in the transparent black panties, her back arched, skirt hiked up, her blonde hair mussed, Oliver’s fingers entangled in the locks as he forced his cock in and out of her mouth.

Frankie was close. This bitch was young, pretty and vulnerable. He knew that she was only cooperating out of fear and terror but that excited him even more. He saw the wicked grin on Jimmy’s face as he stroked Stephanie’s cock through her panties, forcing her to endure the sexual stimulation that she hated herself for experiencing.

“I’m going to blow my load Ollie,” Frankie huffed as he fucked Stephanie harder and faster, pulling her buttocks into his groin as he pounded his cock in and out of her tight orifice.

“Wait for me. Make sure you get this Jimmy,” Oliver hissed as he forced his cock down Stephanie’s throat.

Stephanie didn’t understand what Oliver was telling Jimmy to do, she was just relieved that he had let go of her cock and scooted off the bed. She would realise later and regret it for the rest of her life but for now she was in sensory overload.

Frankie might be raping her but he was doing so with so much finesse that she couldn’t help enjoying the feel of his manhood sliding in out of her tight cleft. His glans pressed on her prostate and his shaft ignited the pleasure sensors along her anal walls and around her sphincter. She didn’t even mind that he was gripping her hips so tightly that his fingers were bruising her flesh.

Oliver bellowed and suddenly Stephanie’s mouth was filled with hot, musky milt which she had no choice but to swallow as Oliver gripped her head still and forced his cock deep inside her mouth. Her anus rippled and undulated involuntarily as Frankie howled and pulled her ass hard into his groin as his cock quivered and filled her tight hole with his scalding issue.

To her dismay and disgust Stephanie creamed her panties. Unable to suppress the wantonness that coursed through her countenance as Oliver filled her mouth with his semen and Frankie’s cock juddered and released in her tight rectum, her body surrendered and an orgasmic seizure wracked her and overwhelmed her. Her panties became soaked with her creamy discharge as she climaxed right along with the men defiling her.

She was given no time to recover. As soon as Oliver removed his penis from her mouth and Frankie’s cock slipped from her battered anus, Jimmy leapt on the bed and rolled her over onto her back. Oliver held her wrists, stretching her arms out to hold her down while Jimmy lifted her legs up high and tore away her panties. He plunged his thick, bloated organ into her dilated hole and began to vigorously fuck her.

The three men raped her repeatedly, using her body as a playground. They forced her to do things she had never dreamed of and to her horror she climaxed repeatedly as the three men illicited pleasure along with the pain. She endured the onslaught for hours until the men were finally sated. They left her curled up on the bed, her costume tattered and cum-soaked, her nylons shredded and her face a mask of ruined makeup infused with cloying semen.

To make matters worse, Jimmy showed Stephanie the video he had taken of her being spit roasted by Oliver and Frankie.

“This will look great on Pornhub,” he sniggered.

“Nah, just kidding. We keep our videos private, so long as the girl keeps her mouth shut, don’t we Ollie,” Jimmy said to Oliver who had just finished getting dressed.

Oliver sat down on the bed and forced Stephanie to look at him.

“Look. We know where you live. We have your phone number. We have the pictures and the video. We can come back and do this any time we want to, so it’s best you keep your mouth shut and we will do the same. See you around toots,” Oliver had the audacity to kiss Stephanie full on the lips.

The three men left the apartment and Stephanie lay on the bed wracked with shame and guilt.

Her anus felt like it was prolapsed, her jaw ached, she had bruises and scratches all over her body but the external damage was nowhere near as bad as the damage to her mentally. In the short term she changed the locks on her apartment and had a security chain fitted and she visited the free clinic and mercifully was found to be STI free but she lived the next few days in constant fear.

The consequences of the sexual assault were immediate and devastating. Stephanie purged.

Purging is a term used to describe a period when a transwoman who is living a double life as male and female suddenly feels overwhelmed and stops expressing her female identity. Stephanie threw away her female clothing and accessories, she deleted all her online accounts; factory reset her laptop and burner phone and sold them to a pawn shop and began to live full time as a man. She moved out of her apartment into student accommodation and cut all ties with her contacts.

Stephanie no longer existed.

Stephen’s grades improved immediately as he devoted himself to study and began to socialise with his peers. He met Mary Granger in his third year of college and they began to date. Mary was very attractive and she dressed the way he liked his women to dress: skirts and dresses, usually with heels. She paid attention to her appearance and always wore makeup and was seldom barelegged, favouring sheer pantyhose or opaque tights.

Importantly she didn’t think it strange that Stephen liked to fuck her while she wore her nylons and would often take her while she was fully clothed. She understood that Stephen had a fetish for her being dressed that way and she didn’t mind pandering to it. She would cure him of that little peccadillo once they were married. He was handsome, wealthy, intelligent, a caring lover and he was going places. He was the perfect catch.

They married right out of college and using his brilliant academic record and Astrid’s family connections Stephen secured a position as an investment banker with a prestigious firm.

The couple made the decision before they were married that neither of them wanted children and unencumbered by family commitments they both worked hard and enjoyed the fruits of their labours. Although disappointed that she didn’t have grandchildren, Astrid Nilsen was happy to see her son settled down with a comely, intelligent woman and to see him become very successful in his chosen profession.

Mary took on a number of administrative supervisory positions before settling down to work at one of the state’s preeminent medical facilities and she enjoyed everything that her life with Stephen had to offer which included a very satisfying sex life. Stephen still had a predilection to fuck her while she wore her nylons and she pandered to his fetish and purchased a small collection of sexy lingerie and exotic hosiery which she wore for him when the occasion suited her.

Stephen and Mary had a very happy marriage and lived in an opulent house in New Rochelle, not too close but not too far from Stephen’s mother. Everything was going wonderfully well, until out of nowhere Stephanie returned.

Westchester County Court – The Trial – Day Two

“The prosecution calls Robert Martello to the stand,” ADA Gerald Thatcher stood stoically behind the prosecution table.

Some members of the jury leaned forward in anticipation of the evidence about to be presented. Large video screens had been brought into the courtroom and positioned so that the judge, jury, defence and prosecution could see them clearly.

The defence had filed a motion to suppress the forthcoming evidence and argued fiercely that the pictures and video found on the laptop and phone discovered in the hidden compartment of Stephanie’s desk were prejudicial and blatantly inflammatory. The prosecution had argued that the evidence supported their view of Stephanie Nielsen’s moral character, establishing a pattern of promiscuous behaviour and bolstered their claim that the defendant and the deceased were involved in a tumultuous relationship and had fought frequently about Stephanie’s philandering.

Judge Vogel had dismissed the motion to suppress but had applied the caveat that nothing pornographic was to be presented openly in her court and the prosecution had been obliged to submit their exhibits to the judge for prior approval before they were presented to the jury.

A short weedy pale man took the stand and took the oath of affirmation.

“Mister Martello will you state your occupation to the court?” the ADA began.

“I am a forensic investigator who works for Doctor Richard Webb, the head of the Forensic Identification Unit. I specialise in information and communication technology,” Robert Martello’s voice was high and whiney and he was the epitome of a geek right down to the pen protector in his shirt pocket.

“Let’s go first to the laptop found hidden in the defendant’s desk in her home study,” the ADA walked around from behind the prosecution’s table.

William Sanford’s chair scraped on the floor as he pushed it back. William was about to object about using the term hidden as it implied dishonesty and unscrupulousness but Stephanie had argued with William during one of their many meetings that denying that Stephanie kept her double life and adulterous activities secret would only inflame the jury once the evidence that supported the claim was presented to them.

Stephanie put her hand on William’s wrist and gently squeezed it, intimating for him to remain seated. Mary Nielsen saw the intimate gesture from where she was sitting behind the defence table and grimaced.

“The Sony Vaio laptop was an older model. I was able to establish that it had passed through several owners before it ended up in the possession of the accused. I established that it had been purchased at a pawn shop three years ago,” Robert said in his squeaky voice.

“It was password protected but I was able to bypass the password in a few seconds,” Robert sounded smug and Gerald Thatcher moved him on quickly.

“Tell us about the emails you found on the device,” Gerald Thatcher addressed his witness.

“The emails were stored in folders. In a folder named ‘Jeremy’ I found a succession of emails. Chronologically they recount Stephanie Nielsen’s first contact with Jeremy Wallace on an online dating site three years ago. The defendant sent a succession of pictures of herself to Mister Wallace and proposed that they meet, and I quote: ‘on neutral grounds’ at a New York hotel sometimes referred to a ‘hot-sheet’ motel. Mister Wallace agreed to the meet and sent pictures of himself to the accused,” Robert used a laser pointer to indicate the text in the emails on the screens.

“With your permission, your honour?” Gerald Thatcher nodded at Judge Vogel who nodded in return.

A series of oohs and aahs rumbled through the court as a succession of pictures of Stephanie Nielsen appeared on the screens. At first she was dressed quite sophisticatedly and presented as a very attractive lady who could easily have been mistaken as a businesswoman. As the slideshow progressed so did the sordidness of the pictures until finally pictures of Stephanie Nielsen dressed in a red bustier, red satin panties, nylon stockings, high heels and not much else, lying provocatively on a bed holding a dildo to her mouth, appeared on the screen.

Stephanie stared stoically ahead knowing that every eye in the courthouse was looking at the screens and then at her.

A succession of pictures of Jeremy Wallace appeared on the screen. He was dressed only in Speedos but the pictures didn’t garner as much excitement as the pictures of Stephanie had done.

“As you can see the two agreed to meet and they exchanged mobile phone numbers,” mercifully the provocative pictures were removed from the screens and screenshots of the email trail replaced them.

“The defendant purchased a prepaid mobile phone at a gas station around the same time that she purchased the laptop. Such phones are often referred to as ‘burners’ because they cannot be traced to the owner,” Robert added.

“As is evident in the email trail, supported by evidence gleaned from the accused mobile phone, the two entered into a sexual relationship and ceased meeting in the motel and began to meet secretly at Jeremy Wallace’s apartment,” a series of emails and text messages flashed across the screen.

Judge Vogel had agreed to a proposal from the prosecution that their witness be allowed to summarise the contents of the emails found on Stephanie’s computer with the stipulation that the defence could object anytime they discerned that the witness’s summation was incorrect.

Having read all of the emails and texts that the prosecution intended to tender as exhibits William Sanford had agreed. He did not want the witness reading the scandalous and provocative emails out loud in the court. The jury were to be given a folder containing hard copies of the email, texts and images for them to peruse during their deliberations.

“And what other email messages did you find?” Gerald Thatcher found it hard to suppress a smirk.

“Another folder was labelled ‘Casuals’ and it contained email messages sent back and forth between the defendant and numerous men. They were themed similar to the emails found in the ‘Jeremy’ folder. Ms Nielsen would receive a response to an ad she had placed on a dating website and if she found the candidate suitable they would exchange pictures, exchange phone numbers and arrange a meeting, usually at a hotel, motel or in some cases at the candidate’s domicile,” Robert Martello pointed to a succession of emails as they appeared on the screen.

“These advertisements that Ms Nielsen placed; can you tell the court about them?” the ADA asked.

The screens flashed again and this time a webpage appeared.

“This is the defendant’s advertisement in the now defunct Craigslist Personals section under Casual Encounters heading T4M,” Robert pointed to the screen nearest the jury.

Mature attractive ‘passable’ transvestite looking for NSA with mature men aged thirty to fifty. See pictures to see what is on offer. Hotel meets or your place, I do not host. NPNC. Discretion required and guaranteed. If compatible we exchange phone numbers and go from there.

Another series of pictures of Stephanie ranging from cheesecake to almost, but not quite, pornographic in nature accompanied the ad and the court got to see them all.

“This is the defendant’s Grindr profile. We found the app on her phone,” Robert continued and the screens changed to show Stephanie’s profile on Grindr.

Stephanie’s Grindr profile was similar to her Craigslist listing and included the obligatory raunchy pictures. Robert Martello had been instructed to delete the pornographic pictures of Stephanie performing fellatio and being sodomised.

“Objection your honour, the defence has already stipulated that my defendant met Jeremy Wallace on an online dating site and that she advertised on other sites,” William Sanford got to his feet.

“Your honour, this evidence is crucial to the prosecution’s premise that the accused had been in a long term relationship with Jeremy Wallace and that they had argued about Ms Nielsen’s promiscuity,” the ADA countered.

“Objection overruled but make your point soon councillor, this courtroom is not the place for show and tell,” Allison Vogel had seen enough pictures of Stephanie Nielsen dressed in lingerie posing provocatively.

“Very good your honour, just a few more questions for my witness,” Gerald Thatcher bowed to the judge to hide his triumphant smirk.

“Please explain the acronyms for the jury,” the prosecutor asked.

“Well NSA means ‘no strings attached’, T4M means ‘trans for men’ and NPNC means ‘no picture, no chat’. These are common contractions used on internet sites,” Robert explained.

“How many men did Ms Nielsen actually meet up with from these sites?” Gerald Thatcher asked.

“That’s impossible to say but putting together the email trails and linking them to text messages in her phone, around fifty men over a three year period. With the exception of Jeremy Wallace it appears that Ms Nielsen only ever met these men once and then the relationships ceased,” Robert Martello explained.

“So based on the email and text message traffic you estimate that Ms Nielsen had sexual encounters with over fifty men in three years,” it was not a question, just the ADA throwing fuel on the fire.

There was murmur around the court when Robert Martello had said over fifty men. Both Stephanie and Mary Nielsen bowed their heads and could not look at the jury or the gallery.

“Moving along, what else did you find of relevance on the devices other than the back and forth messages between Ms Nielsen and her suitors arranging one-off meets?” the ADA was on a roll and ready to put another nail in Stephanie Nielsen’s coffin.

“We found a plethora of digital images and video of Ms Nielsen having sex with men. I have been instructed not to put those pictures on display in court but the jury has access to them for deliberation purposes,” Robert sounded smug again.

“Back to the texts and emails if you please,” the ADA steered his witness.

“Here in these texts and email messages you can see that about a year before he was murdered that Jeremy Wallace was imploring Ms Nielsen to give up her promiscuous lifestyle and enter into a monogamous relationship with him. He even suggests that Ms Nielsen leave her wife and move in with him permanently,” a succession of emails and text messages appeared on the screen to support Robert Martello’ supposition.

“Can you show us Ms Nielsen’s responses to these messages?” the ADA asked his star witness.

“Ms Nielsen basically replies that Jeremy Wallace’s proposals are ridiculous. Although Jeremy espouses his love for Ms Nielsen, Ms Nielsen says that they are nothing more than long-term part-time lovers who find each other mutually compatible and that she has no intention of leaving her wife,” Robert Martello points to a series of email and text messages yet again.