Making Crime Pay

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"I'd like to," he said enjoying the way he looked. "She's hot."

"Yeah, no argument there. But she's a person of interest in the case. If you ever do see her, you call us."

Jason laid low for two weeks before calling the detectives himself. "Any leads?" he asked them.

"Nothing," the detective told him. "Did you think of anything that might help us out?"

"No, I was just thinking I'd like to get out of here. With what my uncle did and all, it's kind of uncomfortable and I was thinking about maybe starting over somewhere."

"That's none of our business, Jason. We just need to know how to contact you in case we need more information."

"Um...well, you have my cell phone and I'll have that with me. I'm not sure where I'll end up, but you can always get me at this number."

"Okay. Sounds good. But if you hear from your uncle or think of anything, you have a legal obligation to call us. Understand?"

"Yes, sir," he said as he hung up the phone.

He'd already packed the few things he'd need then threw them in his car and headed to the cabin. He'd planned on picking up the cash and heading out to start his new life, but his need to see Nate was overpowering. He fully understood that if Nate refused to accept him as Jenna, it was over. Then again, if he wouldn't accept him as her, he didn't much care whether he lived or died so it seemed well worth the risk.

The next morning, he laid everything out just like it had been when Tina was there. He spent the next couple of hours washing, setting, and restyling the long-haired wig before beginning the transformation.

Two more hours passed before he was satisfied that Jenna looked like Jenna as she carefully pulled on the perfectly-styled wig then teasing the roots.

"I really am beautiful," she told herself honestly as she examined her handiwork. She turned sideways in the mirror and felt very happy with the results. She was wearing the very pretty white blouse with the ruffled neckline, a short black skirt, and a very dressy looking black cardigan sweater. Jenna added her jewelry back in then stepped into her heels and took one last look at herself.

"If this doesn't get his attention nothing will," she told herself as she dialed his number.

"Nate? Don't hang up. I need to talk to you." Jason spent several minutes spinning a cock and bull story he knew would convince Nate to drive up to the cabin and although he wasn't very happy about it, he agreed. 'Jason' told him that Emily Cowen, a girl Nate had always liked, was with him and wanted to meet Nate there. He'd hated lying but desperate times called for desperate measures.

Jenna sat waiting nervously until she saw the lights from a car shining from down the dirt road. Her heart was pounding as it pulled to a stop in front of the cabin. She saw her beloved Nate get out and close the door and he was so handsome it hurt.

A moment later there was a knock on the door. Jenna smoothed her long hair, smiled brightly, then opened the door. "Nate? Hi, I'm Jenna. Jason told me you'd be coming."

He looked in and said, "Where's Emily?"

"Oh, she had to run to the gas station back toward town with Jason for something to eat, but they'll be right back. Won't you please come in?"

Nate was hesitant at first but said, "Yeah, sure." He sat his coat on a chair then said, "You got any beer?"

"Yes! Let me get one for you, okay?" Jenna grabbed a bottle of his favorite beer she'd picked up on the way there and opened it. "Here you go," she said smiling at him.

"So how do you know Jason?" he asked, "and why haven't I seen you before?" He looked her up and down and said, "I'd definitely remember you."

Jenna smiled and said, "Nate? I was talking to Jason and well...he told me you guys had some kind of argument or something. He feels really bad about it, you know?"

Nate took a big swig and said, "Yeah, well that's tough shit."

"He really likes you, you know," she said sweetly.

"Yeah, I know," he said taking another drink then belching loudly.

"He said he'd do anything to be your friend again. I know it's none of my business but...."

"There's only one thing he could do and that's not something he can do so let it go, all right?"

"But what if he could?"

"What?" Nate said killing the beer.

Jenna moved a little closer and said, "What if he could do that one thing?"

"He can't. It's impossible." He belched again and said, "You got any more of these?"

She brought him a second beer and said, "But what if he could?"

Nate twisted off the bottle cap, took another long pull. His tone changed as did his face. "That would be like the greatest thing ever," he told her. "Then we could be...friends...again." He looked over at her and asked, "He didn't tell you what we argued about, did he? Because if he did, I'll wring his skinny frikkin' little neck."

"He loves you, Nathan," she said. "He told me that and he said he'd do anything to make you love him back."

"Nathan. That's what Jason calls me. Nobody but him calls me that." He took another drink then look at Jenna out of the corner of his eyes. "Why do you care so much anyway?"

Jenna took a deep breath to calm herself before saying in Jason's voice, "Nathan?"

She watched as he slowly turned toward her. When his eyes met hers she said still using Jason's voice, "Nathan, it's me. Jason. I'm...Jenna now."

"What the fuck?" Nate said setting his beer bottle down. He stood up and walked over to her and started looking at her. He focused in on the eyes and the mouth and said, "Say something else."

"I...I love you, Nathan. And when I said I'd do anything for you, I wasn't kidding. You said you needed me to be a pretty girl for you so...here I am. I love you and I'm all yours."

Nate stepped closer and said, "Wait a fucking minute! You're that...girl...in the robbery video. Holy shit! There's a huge-ass reward out for you! Do you know how much you're worth to me?"

She switched back to her Jenna voice and said, "Everything, I hope. Because I risked everything to try and make you love me." She moved closer and said, "I know you love me, Nathan. But you were afraid to love me as Jason. But I'm not Jason anymore. I'm Jenna and if I'm pretty enough for you now then....you can have me the rest of your life. But we'll have to move somewhere so we can start over."

She stood directly in front of him and looked up into his eyes. "Am I pretty enough for you now?" she asked hopefully.

He ran his hand through his thick hair and said, "Jesus! Fuck! Are you serious? Is this some kind of sick joke or something? Is Emily even here?"

"No," she said softly. "Emily isn't here. I lied and I'm sorry. But this is no joke. Nathan, I'm so in love with you and I've risked everything just to know if you might love me back. So either turn me in or...make love to me." She was looking longingly into his eyes before she could no longer hold his gaze. She looked down and felt a tear fall.

"Hey? What's goin' on with you there? Jason?"

"It's Jenna," she said correcting him while trying not to cry.

Nate didn't know exactly what to do so he hesitantly put his hand on her shoulder and said, "Look. I'm just confused, okay? You called me up here and you spring...this...on me. What am I supposed to do? Ask you to marry me or something? I mean, come on, dude." He paused then said, "Sorry. I meant to say...Jenna."

"I can only imagine what a shock this is to you, Nathan, but I didn't know how else to get you to come to me. I didn't want to lie to you." Her face was now screwed up in pain as she said, "I'm so in love with you I'd rather die than live without you." He just stared at her as she said, "Please! Say something. Anything."

She saw his eyes move quickly between hers before he reached in his pocket and pulled out a small handkerchief and dabbed her eyes. He put if away then put his hands on her shoulders. "This is some crazy shit," he told her before he smiled.

"Crazy people do crazy things, Nathan," she said. "Especially when they're crazy in love."

"You'd live like this for me?" he asked as he gently moved her long hair back behind her ear.

"Yes. I'll do anything for you," she told him sincerely.

"Do you do blow jobs?" he said smiling.

Jenna's eyes open wide as she smiled, too. "Nathan!" she said as though she was deeply offended.

He put his arms around her and said, "So? Do you?"

"For the right guy," she said as she put her arms around his broad shoulders.

"Then I'm in," he said as he kissed her for the first time.

"Oh, my God," Jenna sighed as their lips parted. "This was so worth it."

"Where's the bedroom in this dump?" Nate asked her.

She let go of him then took his hand and said, "Follow me."

When they reached the bedroom, Jenna took both of Nate's hands and said, "I'm not a boy anymore, Nathan. I'm a girl, and my name is Jenna. Can you promise me you'll always treat me like a girl from this moment on?"

Nate took her pretty face in his hands and said, "I will never forget. I promise."

Jenna slid her tiny arms around his neck and gave herself to him. First in the form of a long, passionate kiss, then by slowly undressing him before turning him around and sitting him on the edge of the bed.

Jenna smiled at her handsome lover as she knelt between his legs. "I've dreamed of this for so long," she told him and she reached out and wrapped her small hand around his growing shaft."

"You look beautiful, Jenna," he said putting his hand behind her head and pulling her toward him.

Jenna opened her mouth wide and took her lover's cock into her warm mouth savoring every moment of the experience. She loved the way it looked, how it felt in her hand, and especially the way it made her feel in her mouth. She pressed her lips tightly against him and used her tongue to push as she lowered her head to take him deep.

"Oh, shit!" he groaned. "That's fucking amazing!" he told his new girlfriend.

Jenna slowly raised back up keeping the pressure on. She gently placed her free under his large sack and lifted up, rolling both of his balls in her tiny hand as she sucked and slurped and loved her handsome boyfriend. Jenna softly squeezed his balls and loved the way he groaned as she deep-throated him. She'd practice before with well, things from the produce section, and she was thrilled to learn her practice paid off. She took him as far as she could then relaxed her throat and took him two more inches. She controlled both her breathing and her gag reflex until nature won out. She came up trailing long streams of sticky saliva and gasped for air.

"Fuck me!" Nate said as she used her hand and all of the new moisture as she fought for breath.

"I love your beautiful cock, sweetheart," she told him as she smiled and went back down.

"I wanna fuck you, Jenna," he said.

She came up for a moment to say, "Say 'make love to you' and you can have me."

"Oh, baby. I'm so sorry. I didn't mean it like that. Yes, I want to make love to you. You're so beautiful. How could I not want to?"

Jenna stood and slipped off the pretty cardigan then began unbuttoning her blouse and Nate unzipped her skirt and let it fall to the floor. Jenna removed her panties and padded garment and exposed her shaved body to her lover.

Nate pulled her onto the bed causing Jenna to yelp with pleasure as he turned her over on her back and kissed her. She put his hands on her bra and whispered, "These will be real very soon, my love."

"We'll have save a lot of money, baby," he told her as he squeezed the soft forms in his hand.

"Don't worry about money," she told him. "I just want you to know I'm going to be a woman in every way for you very soon."

Nathan had no idea the money was already there but just the thought of his beautiful girl having real breasts and a warm, smooth pussy made him even harder. He rolled over on top of his beautiful girlfriend who spread her legs wide and lifted them high offering him all that she had.

Jenna told him there was lube in the nightstand which he grabbed and poured generously on himself and into his lover's tight hole. There were also condoms in the drawer and Nate asked, "Do you want me to wear one?"

"Uh-uh," she purred. "Cum inside me so I can feel you and know you're with me, okay?"

Nate pushed slowly and firmly. Jenna gasped loudly as the head popped inside her. "You okay, baby?" he asked with genuine concern.

"I'm perfect," she moaned. "Make love to me, honey," she begged him.

Nathan slowly took her inch by inch backing up then going back in. This was a totally new experience for both of them and when Nate hit something, he stopped but Jenna groaned with pleasure.

"You all right?" he asked again.

"Mmmm. I think that's my prostate gland. It felt really nice when you bumped it. Can you do it some more, please?"

Nathan gladly did just that tapping it firmly many times in a row at the end of each long stroke.

"Oh, God! I'm gonna cum," Jenna cried. "Cum with me, honey!"

Nathan pumped her fast and hard trying to bang her where she needed it. He felt her body tense just before she cried out in ecstasy. "Oh...my...GOD!!!" she screamed as cum shot out from both of them making a mess between their hard bodies and creaming the inside of Jenna's.

Nathan was panting hard as he shot his last stream inside of her. "Jesus! Fuck!!!" he groaned as he held himself over her. "That was amazing!"

In spite of the mess, he lay on top of her and said, "I love you so much. I can't believe you're doing all of this for me."

"Mmmmm. I love you, too, Nathan. I've been in love with you for so long and when you love someone you don't just say it; you do it. And I promise I will have a pussy for you as soon as we decide where to live."

Nathan rolled over and said, "Where do you want to live, Jenna?"

"Somewhere that doesn't get hot," she told him. "I want to be able to go outside without sweating so my makeup won't be a mess."

"Yeah, and I want to get the hell away from here," he told her. "Hey, how about Alaska or Canada?"

"Um, that's a little too cold." She lay there for a moment then rolled over and put her hand on his chest and said, "What about Seattle?"

"Washington State?" he asked.

"Yeah. It doesn't get too hot and it doesn't get cold like Alaska. And they have really good doctors there who can do my surgeries."

"Isn't it expensive?"

"Well, maybe it is but....wait right here, okay?" she said.

She slipped on a robe and went outside. Five minutes later she came back in carrying two large bags and set them on the floor.

"What's that?" Nate asked as he sat up.

"That...is our future life together, my love." She unzipped them as Nathan slid off the bed.

"Holy shit!" he said as he saw the stacks of twenty-dollar bills. "Where did you...."

He looked up at her and said, "That was you. Holy shit...."

"That's why we can't stay here. I need to go to Seattle as Jason and get settled. I'll start letting my hair grow longer and get started on female hormones. Then I'll be ready to live full-time as Jenna with my own dark hair rather than a wig and within a year I can have sexual reassignment surgery and...."

He took her in his arms and said, "And we can get married."

"Mmmm. Are you proposing to me?" she asked with a big smile.

"I believe I am," he said. "I don't have a ring...."

"That's okay. You have my heart and that's enough for now." She pushed him back on the bed and let him take her doggy style this time.

The next morning she told him he'd need to leave and wait for his text. After making love and showering together, Nathan kissed her goodbye and told her how much he loved her.

Jenna reluctantly became Jason again and after packing a few things, drove off for the west coast. Three days later she was in Seattle looking for a realtor, a therapist, and a doctor who performed SRS. Once she was settled, she sent Nate a text. He said he'd be there the next day and Jenna met him at the airport.

They kissed in public for a very long time before going to baggage claim and then to their new home. Nate found a job in construction and Jenna went to work in an office to provide financial cover for their upcoming expenses.

A year to the day later, Jenna was in recovery with two very beautiful, full-C cup breasts and a vagina of her own. She hurt terribly, but it was drowned out by the warmth and happiness she felt knowing she would soon be Mrs. Nathan Jeremy. She smiled as she pictured herself in a long, flowing, beautiful white wedding dress standing next to her handsome husband in his black tux.

It had all been worth it. Every minute of it. As Jenna drifted off to sleep, she smiled and thought to herself, "Sometimes, crime does pay.

Please rate this story
The author would appreciate your feedback.
Share this Story

story TAGS

Similar Stories

Blowback An attempt at mind control backfires. Feminization ensues.in Transgender & Crossdressers
My New Job A college kid undergoes a transformation at his new job.in Transgender & Crossdressers
One of the Girls Eric unwittingly takes a job as a shemale porn actor.in Transgender & Crossdressers
Dream Girl A wealthy young man meets the girl of his dreams.in Transgender & Crossdressers
My Big Sister His older sister has a few surprises.in Transgender & Crossdressers
More Stories