The Law Rises to the Occasion Pt. 05

Franko got to spend Wednesday night and all day Sunday and Monday with his family -- Sunday and Monday because they were considered low sex-traffic days. Franko and Chrissy and their three young children missed each other considerably, and Franko kept saying he hoped his assignment would be over within several months.

Franko always told Chrissy that "it's just another job" and made it sound as though dressing up as Jess was a mighty chore -- one that he put up with reluctantly. Chrissy had certainly seen some photos of him as Jess, taken by Sheila, so she more or less knew that her husband was exposed to a whole new world -- intimately.

"Does dressing up turn you on, dear?" she asked in bed one night.

"Oh, I guess just a touch," he admitted.

"Would you ever want to wear any of my things, now that you're so used to women's underwear?"

"You kidding? I only want to see women's stuff on women. That's it!"

"Just thought I'd ask. I heard from one of my old college friends one time that her husband was into crossdressing. She said it made their sex hotter."

Franko let that go unanswered, as he leaned over to kiss her and put his hand between her legs.

Franko as Jess had quite a few more close encounters with johns in cars, out on the street. She had actually begun to like leading them on, seeing how high she could jack her price up before they gave up -- as a way of gauging her attractiveness. She enjoyed asking what they wanted -- like, "Are you a slow fuck or do you go to the races?" "Would you like to suck my tits or eat my cunt?" "You want to play out a fantasy?"

That last gambit brought some interesting comebacks. One 30-year-old wanted to be tied up, whipped, and fucked with a dildo. A balding guy who looked like a dentist said he looked forward to getting a hand job while watching porn. An obviously gay guy wanted to have a threesome -- two guys and Jess.

One thing was soon evident: At least half the men she negotiated with, she detected, suspected she was a guy. She knew that in online chat rooms, guys talked about their experiences with various hookers. One guy even told Jess straight-on, "Look, I really like sex with a chick with a dick."

To which Jess replied, "Well, big boy, you think I got a dick to stick in your mouth? Tich, tich."

The man began to perspire and get nervous.

"It's OK," said Jess. "A lot of guys want that, you know."

But of course, the man couldn't meet Jess' monetary demands.

So far, after three weeks, no one had attempted to abduct him, force him to do anything, or present the personality profile of a Bellevue-area sex perp. No one had raised his suspicions.

His police backups, although entertained by some of his conversations, were getting rather bored. They also seemed to be smoking dope back in their van.

One Friday night, as Jess suggestively sat in her customary bus-stop bench around 11 p.m., musing about the feel of her nylons, and bra, and long hair, and dangling earrings -- a statuesque woman sat down near her.

She was quite striking, and even too exotic and stylishly dressed, thought Jess, to be a Bellevue sex worker.

"What bus you waiting for?" asked Jess in her best woman's voice.

"Oh, not here for the bus," replied the stranger in a slightly husky voice.

Jess knew instantly she was a guy. Either a guy or a woman who smoked a couple packs a day. No, she had to be a guy.

"You working?" the woman asked. "This your spot?"

"You could say that," responded Jess.

"Well, then, I'll move on. Don't want to step on your turf."

"Don't mind. Not a whole lot of action tonight."

"I noticed."

Jess looked her over more intently. When the "woman" had approached, Jess had loved her curves. She was an appealing Black/Asian mix, she guessed..... thoroughly feminine except for the hint of a deeper voice. "She" had a deep-Southern accent.

"Name -- I mean real name?" Jess asked.

"Naomi."

Jess wanted to further the conversation, but knew that her backups Mitch and Jacob were hearing every word -- at least Jess' words. So she reached into her purse, turned off the electronics, and excused herself to call them to tell them to not worry and go home for the evening. Which they were delighted to do.

Jess apologized, then introduced herself. At that moment, a car suddenly pulled up, and a john inside motioned Naomi over. After a couple minutes of animated conversation, she blew him off.

"What a creep," she said. "Wanted an all-night, but lived in the cheap part of town. He couldn't afford me."

Jess knew that Naomi had seen through her early on, but they kept relating as two women, which was fine by Jess, who, over the past several weeks, had found herself making the gender transition easily. Of feeling womanly. Even though she used to picture himself as 100 percent a tough-guy cop.

He guessed correctly that there was more to Naomi than streetwalker. She confided rather easily that she'd dropped out of college in Florida, tried being a real estate agent, then got involved with a no-good who'd gotten her hooked on a drug -- which one she didn't say.

After she left him, a friend introduced her to the world of big-money call girls. Eventually, she became the mistress of a well-known politician in Tallahassee. When a reporter started sniffing around about the relationship, the representative of the people told her in no uncertain terms to leave town. And now, she admitted, she had hit rock-bottom.

"Thanks for tellin' me all this," said Jess. "I feel for you. What'r'ya gettin' high on?"

"Coke, you know. A little hash."

"Seems like you're too high-class to be working streets here."

"Girl needs money. But I worry sometimes about a guy messing me up, especially when they learn I have a dick."

So there it was, honest and plain as day.

But Jess let that admission pass by. "So where are you staying?"

"I'd been staying at a motel. But they kicked me out today because I'd run out of money. Still got my car. I'll be living out of it for a couple days 'til I make some more money."

The more Jess looked and listened to her new acquaintance, the more attracted she became. Naomi's beautiful features -- eyes, lips, cheeks, breasts, thin wrists and delicate hands -- and her brown complexion -- inflamed him. Even the fact that she was for sale added to the allure.

Naomi added she was of a Filipino/Korean/Black background.

Jess couldn't prevent herself from inviting the woman to stay with her for a few days until she could get on her feet again. It was the "help the poor waif" part of her that kicked in, backed by horniness.

Naomi accepted and they walked to her car a couple blocks away. On the way, Naomi said, "You do pass pretty well, Jess. I mean, I can see how men would want you."

"Thank you, dear."

In the motel room, which had double beds, Naomi unpacked a few things. "Mind if I take a shower?"

Jess ordered some pizza, soon delivered. Its fragrance soon filled the small space.

Naomi emerged with a small towel wrapped around her natural hair, and a large towel covering her tits and midsection. Jess, still dressed, could see the small hint of her dick underneath. With her makeup removed, Naomi didn't look quite as sexy, but she still had that natural, feminine appearance.

Jess couldn't help herself. She went to the tall, brown, willowy woman and slowly unwrapped the big towel. Underneath were nearly natural-looking tits, and an impressive prick, now attaining erection.

Naomi smiled. "Girl to girl," she whispered. "Gurl to gurl."

She removed Jess' skirt and pulled off her patterned panty hose, so as to release Jess' engorged dick. It bobbed healthily in the air as she stood there.

This was certainly looking more and more like a thrilling evening for an off-duty cop.

Naomi squeezed their two rods together, and Jess almost involuntarily began thrusting against her hand.

"Now, now, whoa," said Naomi. "Here's what I need. I need you to fuck me good. I need a good fuck. A real good fuck in my boi vagina."

Jess hadn't counted on this turn of events. "Ah," she said, "you know, I'll say I'm not really into that, baby."

Naomi drew back and feigned shock. "Well, then, maybe I should fuck you? You want that?"

Jess shook her head no.

"Oh, wait," her guest said. "I understand where you're cuming from. Would you mind wearing a strap-on?"

"You mean one of those dildo things?"

Naomi laughed. "You really aren't that sex-smart, are you? Don't feel uncomfortable, baby. Yes, I have a strap-on dildo. You work with that, maybe?"

And so, strapped into a red-leather harness with a long lubed-up red dildo, and with Naomi up on all fours on a bed, Jess approached. Naomi's attractive derriere presented itself, as her cock and balls trailed down below.

Naomi obligingly smeared some lube around her relaxed buns hole, saying, "Do me, gurl; I so want you. Do me."

So Jess, the cop, wearing a bra and wig, found himself/herself about to make an exotic streetwalker happy. If Mitch and Jacob, or, oh god, his wife, saw him/her now! But the dangerousness and sinfulness of entering Naomi was just too powerful.

As the head of Jess' faux penis entered her, Naomi moaned, and reached back to hold her dick. Jess began to slowly fuck away while grasping Naomi's hips. Jess would enter all the way, until Naomi's butt contacted her, and then pull back.

As Jess fucked, Naomi began to stroke own dick, more and more vigorously. After a few minutes she came.

"Oh, god, thank you, my little friend. That was perfect."

Little friend? thought Jess. Little friend?

Now Jess was seeing Naomi as 70 percent female and 30 percent male. That was disconcerting. She wanted her guest to be all female -- with a dick.

"Sometime, if you're into it, I'll do the same for you," said Naomi softly. "You want a fuck?"

"Don't think so."

"Ok."

After Jess went into the bathroom to clean off the dildo and remove the harness, she returned, wearing her good-girl nightie.

They proceeded to devour the pizza, which needed a little warming in the room's microwave. Naomi, who had put on a satin-like slip, proceeded to ask Jess about herself.

"Well, I don't know how you'll take this -- and I could lie and tell you I was a Memphis girl on the skids -- but here's the thing. I hope it doesn't scare you. I'm a cop.... "

Naomi immediately shrunk away. "Get away from me. You had sex with me and now you're going to arrest me. Now it all makes sense."

"No, no, no," laughed Jess. "NO, NO, NO!..... I don't know if you've heard but there are a couple bad actors out there who have raped, or messed up some girls on the street. Even one homicide. I'm a decoy. I'm out there to try to pinpoint who this asshole or assholes are. I didn't want the job, but kinda got forced into it. Heck, I'm married with kids."

Naomi was silent for a minute, then: "So why invite me here? Could get you in trouble. You just want sex or are you a do-gooder or something?"

"I felt sorry for you. I don't think you belong on the streets. You're better than this. I guess I want to protect you. Sure, this is a risk for me. But I've never been a regular cop."

"Well, I'm no angel, Jess, but yeah, I'd like to leave the street life. But I'm strong, and I can make my own way in the world..... Imagine, my being helped by a cop!"

With that, they both watched TV and had some beers. Then it was time for lights out, at midnight. Naomi asked if she could sleep with her benefactor.

"I guess. Actually, nice to have some companionship in this lousy motel."

As Jess flicked the light switch off and crawled into bed, Naomi was right behind her, and with her larger body, spooned and put her arm around Jess, who seemed to welcome the closeness.

As dawn broke through the frayed shades over the windows, Jess woke up to find Naomi's hand migrating down her belly (while under the blanket). The cop didn't resist, and in fact wanted the hand further south. Soon, she felt Naomi's fingers gently contacting her dick, which grew in response. Jess was always hornier in the morning.

"My turn," whispered Naomi, and Jess felt her boobs against her back.

Naomi gently brushed her fingers along the length of her/his manhood, and Jess shivered in anticipation while breathing heavily.

After getting her friend worked up, Naomi maneuvered herself around to Jess' frontside under the blankets and began to lick Jess' penis' head. Soon the tip was consumed by her lively mouth.

Jess moaned.

Involuntarily she suddenly pushed her organ further into her orifice, which made Naomi pull back and sputter a bit.

Jess heard her friend say, under two layers of blankets, "Don't force it, baby. Let me guide you."

So Naomi continued to mouth just the tip of Jess' erection. Soon after, she did gradually consume more of her.

Now Naomi had her long fingers around Jess' penis' and balls' base, and she soon insistently took Jess' dick in and out of her mouth with an expert's skill. Suddenly, again, Jess involuntarily pushed into her several times before exploding into a cacophony of pleasure while pumping his warm milk into her.

After Naomi emerged and went to clean up, Jess confided: "I think you should get a PhD in sex. What you did was so hot."

"Does your wife ever blow you?" asked Naomi.

"Ah, maybe a couple times a year. Special occasions. Maybe my birthday, maybe Christmas, or maybe we saw a movie with oral sex."

"Aw, Jess, you're missing out."

"Guess I am."

Note: Don't miss the upcoming final episode of "Rising to the Occasion."