Cop Town Girl Ch. 01

Chapter One - Penelope

Penelope Bishop gripped the steering wheel so hard that her hands were beginning to cramp. She stared intently at the tunnel of light made by the headlights; the road was sealed but unmarked except for the reflectors nailed to the white posts spaced sporadically along the side of the road. The night was pitch-black and the road was dangerous; besides the soft shoulders and the many potholes, wildlife was often attracted to the bright headlights of approaching vehicles.

Despite the air conditioning the car was sultry; sweat ran down her back and her thighs were sticky with perspiration, she wished she had foregone her pantyhose but they were part of the dress code.

The man sitting in the seat behind her pointed a pistol at the back of her head. It was a Glock 27 .40 calibre subcompact with a ten round magazine and with an overall length of 6.5 inches and width of 1.26 inches it was the perfect weapon for a woman to carry concealed.

Penelope knew everything about the pistol because it was hers.

The man in the front passenger seat held a Berretta 92FS 9mm which he waived around animatedly as he spoke. Penelope hoped the safety was on because the man was likely to accidentally discharge the weapon if it wasn't. He did all the talking whilst the man in back remained stoically silent.

"You see, as a lifelong member of the criminal fraternity I understand that the police department has to abide by those bullshit Equal Opportunity laws. Hence they have to let women run around pretending to be police; they wear the blue pants and shirts, the hats, and boots. They have all that heavy shit hanging off their duty belts weighing them down and they just look stupid. Cute but stupid; especially when they run," the man espoused.

"So the police are now equal opportunity employers; they even had that fat ugly cunt running the show as Police Commissioner in Boston for fuck sake."

"So, as silly and as ineffectual as they are, I can see the attraction for women wanting to become cops. But what I don't get is why some guy changes his sex from a man to a woman and then joins the police department. It makes no sense to me. Even with the stupid fucking Gender Equality Act. If ya wanna be a cop be a man; why pretend to be a stupid woman cop for fuck sake?" the man was half turned in his seat addressing both Penelope and the man sitting behind her.

"Is she a detective or a defective?" he tapped the muzzle of the pistol on the silver shield clipped to the waistband of her skirt and sniggered at his own joke.

He was obviously hoping to get a rise out of her but Penelope gritted her teeth and said nothing. She had met plenty of men who displayed both transphobia and misogynism throughout her life and she was almost immune to such vitriol.

"She's got great tits though," Penelope pushed away the pistol that the man pushed inside her blouse and pressed to her breasts to emphasise his point.

"And legs to die for," she did the same when the man hooked the foresight of his pistol under the hem of her skirt and dragged it up her thighs.

"But has she got a package in her panties or is she a cut-and-tuck? Have you got a designer-vagina sweetie?" the man pushed the muzzle of his pistol into her groin and she angrily wrenched it away.

"That weapon is going to discharge if you're not careful," Penelope hissed through gritted teeth.

"Fuck me! It talks," the man chuckled

"Keep your hands on the wheel," the man behind Penelope tapped her on the crown of her head with the barrel of his pistol.

"Can we fuck her before we kill her?" the man in the front passenger seat asked.

"From what I know about you Bobby, it'd make no difference if she was warm or cold," the other man replied dryly.

"Once the boss had finished with her we can do whatever we like with her. One thing's for sure; she ain't going home," the man said cold-bloodedly.

"I've seen these tranny chicks in pornos; chicks-with-dicks they call them. Hot as fuck except for they have a cock. Not really my thing but I suppose it makes no difference when you're fucking her up the ass," Bobby espoused.

"I wonder if she'll get a hardon when I fuck her?" he pondered inanely.

Penelope had developed a trick that she used to escape such prejudiced virulence when it was directed her way. She thought about something else; she dredged up past memories.

She thought back to how this had all begun.

When the Gender Equality Act was passed by the Federal Government in the early 2020s as a backlash against the Trump administration's draconian laws stripping transgender people and other minorities of official recognition there was much celebration amongst the LGBTI community and most of the general population.

It forbade discriminating against anyone because of their sexuality and gender identity. The same people who had protested against same sex marriage and refused to conduct wedding ceremonies or supply cakes and flowers, the Church of course, and the unenlightened, were bitterly opposed to the Gender Equality Act. When the Supreme Court ruled against several states that wanted to claim an exemption to the Act or to legislate loopholes, the Federal Government tied the laws up in a bow. The recently elected Democrat party President signed an Affirmative Action Executive Order demanding that government bodies 'take affirmative action to ensure applicants are employed, and that employees are treated without regard to their race, creed, color, national origin, their sexuality or their gender identity'.

Penelope Bishop always knew that the she was different and when she was a boy of ten years a psychiatrist diagnosed her with gender dysphoria. The boy's father, a native Texan and a police officer in the Balwyn Police Department, said that no son his was going to be raised a 'homo sissy fag' and walked away from his marriage of thirteen years when the boy's mother supported their son's desire to live as a girl.

Rosemary Bishop took her son to California where people were less transphobic and nobody knew them, she got a good job with her nursing degree, rented a nice apartment and enrolled Penelope Bishop in school.

Penelope loved presenting herself as a girl and was very much a 'girly-girl' who seldom wore pants or boys clothing or participated in male dominated activities. She was no fairy though, and excelled at gymnastics and field hockey; she didn't mind roughhousing now and then but she was attracted to the more feminine activities. She did not display disgust at her own genitalia as most children with gender dysphoria did but she learned very early on how to skilfully 'tuck and tape' and soon became adept at doing so and when supplemented by wearing a gaff she presented a lovely flat pubis. At night or when she was sure there wouldn't be others around she freed her genitalia to prevent any complications.

Penelope's psychiatrist assured Rosemary that Penelope was like many other gender dysphoric people; she did not want to fully transition and was happy to live as a transgendered woman rather than have sex reassignment surgery. When Penelope was fifteen and the other girls in her class were developing breasts, she did however desperately want breast augmentation and Rosemary was happy to approve the procedure knowing that it was reversible. She also allowed Penelope to get a tracheal shave and to have surgery on her vocal chords to keep her voice feminine because it had started to break.

At school Penelope was readily accepted as a transgendered girl and made no attempt to hide the fact; there were quite a few male to female and a few female to male transgendered kids at the school. They did have to undergo regular counselling however and were closely watched by the faculty to ensure they weren't bullied or discriminated against.

When Penelope went to college things became more complicated. There were always going to be some people who didn't understand her or were just downright prejudiced but by now she had learned to deal with people like that; it was nearly 2030 and if they hadn't lost their prejudice by now they never would.

Penelope had not developed the identity development problems that are common among some transgendered people, but one of her biggest issues was her burgeoning libido. Advances in hormone therapy using supplemental pharmaceuticals that assisted with the feminisation process but did not have the adverse effect of suppressing the sex drive were now being commonly used and Penelope was frustrated.

Rosemary had had 'that talk' with Penelope but it was difficult because Penelope was neither female nor male. Penelope obtained most of her sex education on the Internet from TG support websites but she had to admit that she learned mostly from transsexual porn sites. Penelope had plenty of male, female, and transgendered friends and representatives from all of these genders had shown an interest in her sexually; she was mostly attracted to boys but found certain women and transgenders sexually attractive too. She discussed her dilemma with her psychiatrist who advised her to take her time and not rush into having sex.

Thus it was that Penelope believed she was the only student at the University of California who was still technically a virgin at twenty years old. She thought 'technically a virgin' because she had given and received plenty of blowjobs and was quite adept at fellatio, but she had not yet been penetrated and longed to experience the ultimate in sexual gratification. To put it bluntly she wanted to be fucked.

She was close to completing her law degree when things got heated at home. Rosemary was putting pressure on Penelope to fully transition and not to live in limbo as a transgender. To Rosemary's thinking there were only two genders, she was sympathetic to Penelope wanting to live as a woman, but not as a transwoman. She thought that by now Penelope would want to either fully transition or revert back to being a CIS male.

"Honey, you would be so much happier as a woman. You really are already are a woman except for one thing," Rosemary bought the issue up again over dinner.

"I'm happy as I am mom; why do you keep hounding me?" Penelope sighed.

"I'll be honest honey; because then I would have a daughter. I mean I still think of you as my daughter but you aren't really are you?" Rosemary resorted to her usual defence.

"You want me to be a 'real woman' mom? What you are saying is that you want me to cut off my dick!" Penelope was becoming angry.

"Don't talk like that in my house! You know what I mean. I want you to complete your sex reassignment surgery and identify as a woman," Rosemary tried to temper her tone.

"But I like living this way. I have my own opinion and you know it. Not all transgendered men who have sex reassignment surgery feel that they have become women; some are very unhappy and consider themselves feminised men, counterfeits, imposters or impersonators of the sex they so desire to become. What I'm saying is that getting a cunt will not buy me happiness; it's not like I'm going to give you grandchildren! I'm happy as I am," Penelope had never been so forthright and disrespectful of her mom.

"Oh my god Penelope you sound like a TERF! I've been through all this because of you; I gave up my marriage, I moved away from our home town to support your transition, but you're just stalled," Rosemary had never been so outspoken before.

"So what are you saying mom?" Penelope had put down her law book and was so angry that she was crying.

"Oh, shit or get off the pot for fuck sake!" Rosemary stormed out of the kitchen, went to her bedroom and slammed the door.

Penelope was even angrier than her mother was; she stormed to her bedroom, locked the door, threw off her clothes and went into her ensuite bathroom. She took her douche and filled it with warm water and douched herself; she'd had plenty of practise because even though she was a 'virgin' she had plenty of sex toys that she regularly used on herself. She brushed her teeth, showered and combed her long blonde hair.

She was a woman on a mission and she strode into her bedroom and threw a pile of clothes on the bed and then sat down and did her makeup. She applied heavy makeup with lots of black eyeliner, mascara, many hued eyeshadow, rouged cheeks and ruby-red lipstick. She teased out her hair and looked at herself in the mirror; she looked like a nineteen-eighty porn star, exactly the look she wanted.

Penelope stepped into a pair of black Vintage Lace Spanx panties that not only looked good; they would hold her tuck in place as she had no intention of taping. She pulled the panties halfway up her legs and then pushed her testes up into her inguinal canals and stretched her empty scrotum and penis along her perineum; she pulled the Spanx up tight and they held everything nicely in place. Next she slipped into a pair of flesh-toned ultra-sheer hold up stockings. She smoothed the wrinkles out of them and enjoyed the feel of their silkiness on her freshly shaved legs.

She put on a sheer black brassiere that looked sexy and also gave her B-cup breasts support, not that they really needed it. She slipped into a black, figure-hugging, cotton-spandex, micro-mini cocktail dress with sheer back and sleeves, she accessorised with gold earrings, necklace and bracelets and stepped into a pair of four-inch black high heels. She spun around in front of the mirror and was very happy with how she looked.

Emptying the handbag that she took every day to UC Berkeley Law School onto the bed she sorted through the jumble and tossed the essentials into a stylish black leather clutch purse with gold hardware. She took out a menthol cigarette, lit it, and tossed the cigarettes and lighter into her clutch and sashayed out the door; she was a woman on a mission.

When Penelope stopped in the hallway to collect her car keys Rosemary came out of her bedroom.

"Where are you going dressed like that! Are you smoking?" Rosemary was still angry.

"You wanted a real daughter mother, well I'm going to behave like one for you. I'm going to get laid!" Penelope snatched her keys off the side table and went out the front door.

Kyle Beamish had been coming onto Penelope ever since she started at UC. Penelope resited his advances, figuring he wasn't serious and really just wanted to experience 'fucking a tranny'. Still, he remained one of her closest friends and whilst she had been tempted to toss him a compensatory blowjob, she'd decided that it would get in the way of their friendship and send mixed messages.

She pulled up outside of his ground floor studio apartment, part of the off campus housing complex, and noted that he had turned on the security lights for her. He didn't know why she was coming around, but she had texted him that she was on her way and he was prepared for a marathon study session now that they were so close to attaining their degrees.

He was shocked when he opened the door and saw how she was dressed.

"You got anything to drink in this dump?" she pushed him in the chest one-handed and as he staggered back she walked past him into apartment.

"I dunno.. I mean yes.. Sure.. Just let me..." Kyle stuttered; absolutely taken aback.

"Or we can just fuck and you can get me a drink after," Penelope pulled Kyle into her arms and started to kiss him.

He soon got over his shock and any reservations he might have had and wrapped his arms around her and kissed her back. They kissed and groped each other as Penelope guided him backward towards his bed. He broke their embrace briefly to swipe the clothes, books, snacks and other sundry items that bachelors tend to keep on their bed, onto the floor.

Penelope pushed him back on the bed and straddled him; she looked down at him with her green eyes and he looked up at her bewildered.

"You know I have always adored you; you are so beautiful," he smiled up at her.

"I'm not here for adoration Kyle; I just want my cherry taken," Penelope glowered down at him.

"I can do that too," Kyle swallowed.

Penelope lowered her face to his and they kissed, softly at first but soon became frenzied; Kyle was dressed only in his boxershorts and t-shirt and Penelope broke the kiss and ripped off his t-shirt but remained straddling him.

She lowered her face to him again and kissed him while her nails raked his chest.

"Oh, my god I've dreamed of this," Kyle mumbled through crushed lips.

Penelope's hand strayed to his shorts and freed his already rampant erection; she stroked it, massaging the pre-ejaculate into the hard flesh. Kyle bucked underneath her and lifted her dress; she bent down and straightened her arms so he could pull it off her. He unclasped her bra and when her firm breasts fell free he pawed at them, tweaking her swollen nipples; she leaned forward and guided his face to her breasts and Kyle enthusiastically suckled them.

She cradled his head against her breasts while he nibbled and sucked on her nipples and she reached between their bodies to stroke his hard cock. She could sense his urgency and she was impatient to feel him inside her; her spanks were stretched as her tumescent penis became untucked. Kyle tentatively reached out and touched her hard flesh encased in the satiny spandex; a little globule of pre-seminal fluid leaked through the fabric. He scooped it up and bought it to his lips.

Penelope reciprocated and milked a bubble of pre--ejaculate from Kyle's erection and licked it. They smiled at each other lecherously. They both took a beat to shuck out of their underpants; Kyle was naked and Penelope was left dressed in only her stocking and heels which Kyle begged her to leave on because she looked so sexy.

"You want me dressed like a porn star?" she teased him.

"I just want you Penelope," he sighed.

She lay down on the bed and Kyle got on top of her; pressing his body against hers as he kissed her. Their cocks rubbed against each other, the precum making them slippery and delightfully turgid.

"I like that," Kyle whispered.

"Frottage," Penelope smiled up at him.

"What?" Kyle rubbed his cock against hers.

"Frottage; it's French for rubbing cocks," Penelope giggled.

"What is the French for this," Kyle slipped his cock between Penelope's buttocks and placed the glans against her sphincter.

"I think it's called fucking in all languages," Penelope smirked.

She opened her legs and lifted herself up to help him. He pushed forward and his glans entered her pre-lubricated tight ring and she gasped. He stopped and let her get used to the thickness of it.

Penelope had used plenty of toys on herself but the feel Kyle's hard flesh penetrating her was different; there was a little discomfort at first but it felt nice. She could feel the girth of his penis, his hard but still pliant flesh, she pushed herself upwards and Kyle sensed her need and thrust forward ever so slowly.

His cock was gripped tightly by her anus despite the lubrication; it clung to his manhood and felt like a velvet glove. He had to concentrate really hard to prevent a premature orgasm.

Penelope put her arms around him and locked her legs behind his back, instinctively rubbing her stocking-sheathed thighs on his flanks knowing it would stimulate him. Kyle pressed his lips to hers and slid his tongue into her mouth as he slid the remainder of his erection inside her tight anus.

She gasped with surprise and delight; being filled with Kyle's hard manhood was such an exhilarating and illicitly pleasurable experience. They began to rut, taking pleasure from each other as they kissed and fucked. They increased the tempo and Kyle's glans pressed on Penelope's prostate radiating intense pleasure through her anus and into her penis which was rubbing on his belly. Kyle could feel the heat from her cock; she was leaking precum on his flat hard belly. Far from him finding this repulsive, he found it extremely arousing.