Jake Matthews

Jake Matthews is the original name of a person who became known as Ashlyn Shelley after staying at the Inn in 2006.

Background
Jake was born in 1972, a native of the suburbs of Dallas, TX. His parents died three weeks before his sixteenth birthday, after which he lived with his paternal uncle until he was 18. The uncle was a traveling salesman and thus rarely around, and drunk much of the time when he was. He describes himself as never being able to keep a relationship for longer than a few months. He worked as a self-employed 3D animator and motion graphics designer, working on commercials and corporate videos. At some point he was involved in a relationship with a woman named Kim Swanson, who was apparently only interested in his money.

He met Art Milligan through online forums and accepted his invitation in summer of 2006 to visit Old Orchard Beach, Maine, when the proprietor of the Inn refused to rent Art the two-bedroom suite solo. After having a great deal of difficulty arriving at the Inn, Jake was relieved to find the New England weather favorable compared to the Dallas heat. However, he was the first to note that the previous visitors to the Inn had left their luggage, although Art indicated he had already noticed.

After enjoying the Beerfest for a few days, including an awkward flirtation with a German beer server, Jake struck up a game of poker, which he found to be a good way to break the ice with people from all walks of life when traveling for business.

Transformation
In the early hours of August 31, 2006, Jake woke to hear screams emanating from elsewhere in the inn. He bolted upright to find his hair had grown long and red, and that a pair of female breasts had sprouted from his chest. He also noticed a shift in his senses, describing the bed as suddenly feeling harder, with rougher sheets, colder, and with a more noticeable odor from the pile of (his own) clothes. He initially held out hope that the transformation was just a mass delusion, but was disappointed to find his new female appearance confirmed by the clerk of a nearby store.

After a few days of uncertainty, Art informed Jake that they had specifically become the previous visitors to the inn: that this body belonged to a  woman named Ashlyn Shelley. Jake learned further details through a video left by the original Ashlyn, including that she was 23 years old and a native of Cambridge, Massachusetts. She worked in promotions, mostly for radio stations, and had an ex-boyfriend named Josh. Jake was very dismayed to learn that Ashlyn had left various financial problems, with several bill collectors leaving messages on her phone, as well as roommates requesting her share of the rent.

First Impressions
Jake arrived in Cambridge and met Ashlyn's four roommates, Logan Stiles, Dean Williams, Billie Fraser and Jordan "J.J." James. At first he embarrassed himself with his lack of background information on each of their lives and relationships, generally seeming spaced-out and ditzy, not even knowing where the plates were kept. Ashlyn's suddenly-serious demeanor was also confusing to the roommates. He managed to endear himself to the group, however, by taking control of a BBQ they were hosting, using his Texan knowledge to grill demonstrably better than the Massachusetts natives.

In late September, he and Art made a return trip to the Inn, where he met the man who now inhabited his body, Stephen Jefferies. They discussed the details of Jake's work, and compared notes on their transformations. Jefferies offered Jake a chance to come to Dallas and work "for him," but showed his true colors by immediately making a sexual advance toward Jake. Jake soon found that Stephen had indeed gone back to Dallas, "stepped into [his] life" and transitioned from a self-employed position to a managerial one, even resulting in increased client satisfaction.

Employment
Jake made attempts to solidify Ashlyn's employment situation, but found it difficult. College students had taken most of the jobs she was qualified for, with secretarial or receptionist work being out of the question due to a lack of typing ability on Jake's part, and he found many employers reluctant to hire someone with Ashlyn's appearance: "If a woman is attractive, has big boobs, sexy green eyes and long red hair then she must not be very smart. People assume that a woman like that has never had to work very hard because she is has been given everything in her life ... One woman was honest enough to tell me she thought I would prove to be too much of a distraction to the other employees." Her first paying job was in promotions for WBCN, dressing as eye candy and handing out calendars at football games.

Through Josh, Ashlyn was given an opportunity to interview for a waitress job. Jake found that, as Ashlyn, his physical attributes made him a good fit. Looking the way Ashlyn did, combined with an outgoing personality, he was able to make ample tips. On one occasion, Jake accepted (after some consideration) an offer to show his breasts in a private room for a $500 tip, an act for which he later felt regret. However, one of the customers was the manager of a strip club Ashlyn had at one point auditioned for. He had received a gift certificate for the restaurant from "A Secret Admirer," postmarked to the address of the Trading Post.

Romance
Upon meeting Ashlyn's ex-boyfriend, Josh, Jake was sympathetic to his plight as a man in love with a woman who did not return the feeling. Instead of rejecting him outright, he explained that "Ashlyn's" life was too much of a mess to consider a romantic relationship at the time. Josh accepted this, but still left Ashlyn a parting kiss, indicating his continued interest. They later encountered each other a second time when Josh arranged an encounter at a dance club called "Dad's," where they spent the evening drinking and dancing. Jake admitted, despite not considering himself attracted to Josh, that feeling his hands on Ashlyn's body made him feel like it was "on fire," and they proceeded to publicly make out. Jake was shocked to find himself at Josh's apartment the next morning, but was assured it was completely innocent: Jake had lost the keys to Ashlyn's apartment. He later continued to experiment with Ashlyn's sexuality, trying on her lingerie in his spare time, appreciating the vision of her body in skimpy clothes, and enjoying a healthy bout of masturbation after overhearing Logan and his girlfriend having sexual intercourse in the other room.

After deciding to work out regularly in order to maintain Ashlyn's appearance, he accompanied Logan to the workout room at the fire station. Though somewhat annoyed by the attentions of the firemen, Jake did find himself regarding Logan's body with interest, thinking about how "good-looking" he was. This led to much embarrassment and internal confusion over this was just casual acknowledgment from one guy to another, or genuine attraction.

Upon returning from his first workout session, Jake found that he had received a bouquet accompanied by a card: "Lilac roses symbolize love at first sight. That is why I sent them, I’ve wanted you since the first time I saw you, from your secret admirer." Though appreciative of the scent, Jake was unimpressed by the gesture, calling it a waste of $125, but was spooked by the card's PS, which read "I KNOW THE REAL YOU."

When Jake was bedridden with a cold in late October, Josh was not hesitant to offer help, bringing clam chowder, lattes, medicine, and a movie ("Hitch.") the two fell asleep in bed watching, and in the morning Josh asked whether it was possible for them to "go back" to the way things were before things got serious between them, when they were just having fun. Jake was conflicted, noting that dating had not interested him since becoming Ashlyn, but that he was having complicated feelings that he wanted to sort out. He gave Josh a spare ticket to a Halloween costume party he had acquired through work with WBCN.

Over the course of the last weeks of October, "Ashlyn" was sent two more gifts from her secret admirer: a bottle of perfume ("A new scent to go with your new look") and, more unnervingly, a pair of boots, in the correct size, that went with the costume Jake had bought, a sexy pirate wench.

Jake invited Josh along to Ashlyn's family home in Providence for Thanksgiving, but soon found himself uncomfortable with how close he had let Josh get. After hearing from Logan that Josh intended to ask Ashlyn to a New Year's Eve Gala, he worried about how to put him off, being relieved to hear from, of all people, the real Ashlyn. As Jean-Michel, she requested Jake's company at a New Year's event in Montreal, acting as arm candy and giving them a chance to interact.

When in Montreal, Jake pretended to have already known "Jean-Michel," letting him kiss him and acting familiar in case they were being bugged. After the event, where Ashlyn met Elizabeth as Marie, they returned to Jean-Michel's apartment. Jean-Michel helped Jake confront some of the conflicting feelings he had had, as a woman, towards men, as well as toward him - rather, herself, asking the now-woman to describe what she saw in the mirror: "a beautiful woman." Soon, they found themselves making love enthusiastically.

Staying as Ashlyn
In Montreal, Ashlyn as Jean-Michel revealed that he intended to stay in his new life, and expressed hope that Jake would remain as Ashlyn. Although initially reluctant, she found that Stephen Jefferies had taken a liking to his new identity. Weighing all the possible options, Jake concluded that he should remain as Ashlyn, having both grown accustomed to the particular life, as well as wary of having to adjust to a new identity again and relinquish this one to another hapless Inn victim. Jake officially adopted the identity of "Ashlyn Shelley" as his - now her - own - in January of 2007. She set about straightening Ashlyn's financial situation, looked at summer courses, and resolved to get more comfortable with the "opposite" sex.

Around this time, Ashlyn met Matt Armstrong, a neophyte firefighter during one of her workouts with Logan. After spending some time together, she agreed to a date with him. They went out twice - once to a bar, then to a Celtics game - before engaging in sexual congress, which Ashlyn noted was somewhat less thrilling than her first time, with Jean-Michel, but gave Matt the benefit of the doubt, that he did not have the same knowledge of Ashlyn's body. The two continued to date, and eventually Ashlyn became comfortable with the idea of being someone's girlfriend.

Around this time, Ashlyn received a new gift from her "secret admirer," a pink Vespa, which prompted her to consider contacting Jessica, for her professional expertise. Jessica advised not to keep any gifts, as it would merely empower this person.

In April, Jean-Michel visited Boston on business. He and Ashlyn scheduled another rendezvous, after which he revealed he, too, had had a "secret admirer" at one point, who provided cash and a vehicle. He expressed the belief that this person was helping them "establish" their new lives.

In June, she auditioned for a job at Headlights, a Hooters-like restaurant where waitresses were expected to be vivacious, flirty and physically attractive - a job that Ashlyn was visibly ideal for, but left her lamenting the loss of her old occupation. Still, she found her new job to be lucrative, albeit with a certain risk of coming into contact with exceptionally creepy guys. As life went on for Art and a hose of newly-transformed Inn victims, and as Jessica embarked on her road trip with Louisa, Ashlyn, or 'Lyn as those who knew her secret often called her, remained in Boston and continued her relationship with Matt, telling him she loved him in late Summer '07 and agreeing to move in with him.

Though she had some trepidation - mainly fears that the relationship would be unequal, with her as the "neat freak" who has to clean up after the "slob," the move occurred in November, once Ashlyn was able to find someone to take her old room as well as letting Matt's roommate part on good terms. At this time, her Secret Admirer sent her a sextape featuring the original Ashlyn and an unknown party, along with the lingerie worn by Ashlyn in the DVD, and a note simply saying "Something your boyfriend would enjoy seeing."

Appearance
Originally, Jake was of average height, nondescript looks, and husky build, later noting upon seeing his body from the outside that he could stand to lose 30 lbs. His first impression of his new body was that it was "so hot—I’m all tits, hips and red hair." Art attested to this, saying he wouldn't mind seeing Ashlyn in a bikini.

Personality
Jake is, at least at first, an introverted, pensive individual. He notes his tendancy to mull things over until he is sure what he thinks of them, resulting in an occasional delay between events and his being able to write about them. He describes himself as a workoholic, not requiring much sleep, something that changes after his transformation, as he finds himself sleeping until noon occasionally. He is shy around women.

As Ashlyn, he finds himself becoming more outgoing, gradually, as he acclimates himself to the difference in lifestyle that comes with his physical transformation. He becomes interested in make-up, citing it as just another form of art he can do, as well as fashion, largely due to the selection available and his preference for seeing himself, in Ashlyn's body, in a variety of clothes. His interest in taking care of Ashlyn's body also led to him working out on a regular basis, something he was unable to find time to do as Jake. Art notes that Jake "goes native" relatively quickly, but softens this opinion by admitting he has a better feel for the "outside activities" of womanhood. Jake described himself as a "neat freak," whose tendencies were increased after becoming Ashlyn, owing partly to an increased sense of smell.

As a Texas native, Jake's favourite foods from his original life were BBQ (particularly steak and beef,) and Tex-Mex. After becoming Ashlyn, he noticed his appetite getting smaller, and while not losing his love of Texas foods, he gained an appreciation for Clam Chowder and Lattes. He enjoyed girly drinks, and became nostalgic upon drinking a margarita. As Jake, he had gone five years without getting sick once, but was bedridden with a cold within 2 months of being Ashlyn.

Quotes
"Maybe I should have stopped and asked for directions, but what can I say, I’m a guy."

''"Would you mind describing me? What I look like? Be as honest as you can." His eyebrows go up. He looks me over for a moment. "As honest as I can?" "Please, be brutally honest." I say. "I see and incredibly hot redhead with a killer body, dressed in her boyfriend's clothes. That help?" "Yes." I say. "I’m not crazy."''