Chasing Waves Ch. 01

Diego Quinto was an Air Force staff sergeant on vacation leave in Hawaii, his reward for coming back alive from a six-month deployment to the worst place imaginable. There were images in his head that would never go away; not with alcohol, or pills- no, he needed to return to his happy place.

Diego had heard of the transgender culture of a particular street, where military men would go for a blow job or something inexpensive. But Diego wanted more; the Texan wanted to be dominated, he wanted to be fucked. And for $150 he found a long-legged blonde, with eyes like the ocean and lips the color of a cherry Icee.

"You're eighteen, right?" The tall blonde woman asked as she leaned into his open car window. She wore a denim miniskirt, with her panties clearly visible, and a certain appendage slipping out the side. Jolene was clearly older than him, but her face was youthful, sweet, and beautifully feminine, even with the minimal amount of makeup she wore.

"The age of consent in Hawaii is sixteen," Diego replied with a Cheshire-cat smile. He was twenty-five, with a ballbusting girlfriend waiting for him stateside. But at that moment all he had on his mind was the address of a nearby hotel he had already checked in a gotten a key. He figured if he was unsuccessful in finding a partner willing to go all the way he could still use the room to jerk off and get shit-faced. "What's your name, Chica?"

"It ain't Chica, Don Juan."

"What is it? What do I call you?"

"Jolene," she replied as she climbed into the passenger seat of his rented Honda.

"Jo-what?"

"Jolene, Joleene, Joleeeeene," she sang in a voice that was the perfect combination of latina sexy with a country drawl. "Oh, I'm begging of you please don't take my man."

"Oh, you're THAT Jolene?" Diego chuckled.

Jolene laughed. "Smart ass: just for that, I want payment upfront."

"That was the plan." Diego already had a keycard, knowing he would be so hard, he would need to go straight to the room. He parked the car and looked at Jolene while fishing the wad of bills from his wallet. She was looking out the window so he took a chance and stroked her hair, then kissed her neck. "You smell like a pina colada."

"It's what the clients expect," she said with a flirtatious giggle, leaning into his touch. "If I smelled like Versace no one would take me seriously as an island girl." Her speaking voice was truly impressive. She had the voice of someone in the process of transitioning; soft and distinctly feminine with a hint of an accent and just enough depth of tone to betray her birth gender.

Diego chuckled and moved his hand to her thigh. "Versace?" he wanted to ask where her accent was from. It was clear she had class; how did a girl like her end up turning tricks in Hawaii?

Jolene took his hand, moving it closer to her crotch. "We can fuck here, in the car if you like."

"Nah, chica," Diego moaned, "I've got plans for you- for us."

The way she looked at him made his heart race. Her eyes were the most exotic green he had ever seen, like a movie star from another world. "What are you looking at?" she licked her glossy lips and batted her fake eyelashes.

All he could do was smile. Diego couldn't even remember the last time his girlfriend looked at him with such passion. even if she was faking it, she was good. "Room 204- I'll leave the door unlocked."

She bit her lip as if stifling laughter.

But Diego didn't care. He climbed the stairs, entered the room, turning on the lights. He paused for a moment before unlocking the door. The energy of the moment was palpable. The young soldier's body was about to combust at any moment if he didn't strip himself of everything holding this raw power at bay.

Diego was already half naked as he laid on the bed. He pulled out his cock and started to jerk off using only his sweat for lubrication.

Jolene followed at her own pace. He figured her silver platform heels probably weren't ideal for speed-walking. She shut the door, locked it, and joined him on the bed. "Cool down solider. you've been on deployment or something?"

"God, I wish." Diego bit his lip and closed his eyes. "When I was deployed to Afghanistan, I let my men run a train on my ass." It was the truth, his time on deployment had been a non-stop orgy. He could feel the pre-cum on tip of his cock just thinking about it.

"Your men?" Jolene chuckled. "You're just a baby." She started to undress, removing her shoes then unzipping her skirt.

Her cock as big, perhaps even bigger, than his own. And he couldn't wait to take it for a ride. "Nah, I got a baby on the way."

"You don't sound too happy about it. You going to marry the condom-breaking bitch?" Jolene teased as she took his free hand and placed it on her abs. Jolene's stomach was flat, slender. With her mid-drift showing it was clear she didn't have an hourglass figure. He had seen performers fake a female figure with corsets, some even removed ribs. But Jolene was just strong.

"It takes two to tango." Diego sat up, just enough to cop a feel of her ass.

"Yeah, it does." She slipped off her panties, kicking them to the floor. "You like what you see?"

"You know I do." Diego gripped her hard, pulling her close as he took her cock in his mouth. The thick uncircumcised member slid effortlessly down Diego's throat.

Jolene ran her fingers through his hair, giving it a soft tug. "You are so good, it's almost a sin to tell you to stop."

Diego touched her inner thighs, her body was trembling. Jolene sucked cock for a living but it had clearly been a while since she received the pleasure.

She fucked Diego's throat a few more times before pulling out, then dragged her lubed cock over Diego's lips as he smiled.

"I want you on your knees." She stripped off Diego's belt, pants, and boxers. "Your body is like an amusement park," she moaned as she tied his hands together with his belt. "Keep your hand in front of you." she stroked her finger along his muscular thighs, up to his balls. Jolene gave his ass cheek a tender kiss. "I know what I want; I'm going to pound your thick ass hard while I jerk your cock."

Diego couldn't help but laugh. "Do your worst."

"Maybe on our next date." Jolene grinned as she took out a condom.

Diego cringed a little at the sound of the condom wrapper. But he was quickly sated when she started to work her saliva lubed fingers into his hole. he leaned into her, forcing her to go knuckle deep. She was massaging in a way that was making him weak in the knees; so much more than his girlfriend ever did for him.

But he wanted her cock. He could feel Jolene's erection pressing against his skin. She was hard. she wanted him, but something was holding her back. "I can tell you're not into this."

"Don't fucking insult me." She gripped his testicles hard.

"You just don't seem like someone who's used to being on top."

"I'm always on top." She thrust into him with her entire length, with no regard for being gentle. "You like that?"

"Yeah, oh yeah! Fuck me hard." With every thrust, Jolene smacked Diego's ass cheek. But her pace left something to be desired. "When's the last time you were the man?"

There was an awkward pause.

"Fuck you." Jolene pulled out and gave him one last slap to his thigh.

Diego chuckled and rolled over, shimming out of his wrist restraints. His cock was hard, pressed against his stomach and partly covering a tattoo: the word 'Vato" in block letters.

"Vato," Jolene said with a smirk. "You know that word just means, 'friend', right? It just sounds like some ghetto shit."

Diego laid back, licking his palms. "Yeah, I'm not going anywhere. You can suck me off or you can just watch- doesn't matter to me in the slightest." Diego had the word "San Antonio" across the top of his stomach. As he arched his back, his body displayed the words "'San Antonio Vato,' accompanied by black and gray images of flowers, skulls and other typical tattoos that could be created with homemade pens.

Jolene only laughed. "Damn, you have some ugly-ass tattoos."

Diego smiled. "You have any better ones?"

"I do." Jolene took off her low-cut top, revealing her padded bra. She had neither top nor bottom surgery. But what she did have was an elaborate rosary tattooed down the side of her ribs, extending down to her hips.

"Nice," Diego said in a moan as he motioned for her to lay beside him.

Jolene placed her hand on his, and together they finished him off. "You're lucky you're so fucking gorgeous."

"And you're so fucking talented," he teased in response. Diego moved his hand lower to finger his own ass, as Jolene worked his shaft.

"You are such a freak." She moved her fingertips to the head of his cock, playing with his precum. But to Diego's surprise and delight, she finished him off with her mouth.

He shot his load, not even bothering to hold her head in place. He knew she was having as much fun as he was.

When she was finished she licked her lips. "Yum," Jolene said in an adorable, flirtatious, voice as she made herself comfortable on the pillow next to him.

"You want to know why I am the way I am?" Diego leaned over and kissed her on the lips. "Fear can do beautiful, powerful things."

"Fear? You talking about prison or something?"

"Nah," he said with a laugh. "That would have been my future if not for the love of my family and my people. While some were shooting up, getting high- I sought out a higher power."

"God?"

"The power of fucking and cumming, with a little pinch of exhibitionism."

"You flash your cock in public?"

"The secret to a true exhibitionist high is getting a room full of guys to flash their cocks."

"Tell me more."

"On my first deployment as an NCO. I caught one of my men jerking it to a picture of his girl."

Jolene shook her head at the absurd direction of the story. "Ok, what did you do?"

"I asked if I could join him. It was just like holding a conversation with someone at the gym. We talked, about life, out hopes and fears. Then I helped him out a little." Diego cocked his head with a sly smile.

Jolene licked her lips, clearly into his kind of crazy. "Do tell, Vato."

"I massaged his chest, shoulders, and then we kissed," Diego whispered the next part in her ear. "We made love."

"You made love?"

"Raw, bareback," Diego mumbled. His spent cock was soft but he wanted so badly to touch himself. "The next night there was a surprise waiting for me."

"A gang-bang?" Jolene asked, her voice still held a hint of laughter. "That's kinda hot. Did you have a cock mouth and another in your ass?"

"Gang-bang, orgy- whatever you want to call it. We shared a deep profound connection."

"I get it; you shared your strength, like how the ancient Greek warriors used to have sex with younger soldiers. Greek or Roman, it's been a while since I took a history class."

"All I know is; what happens on deployment stays on deployment," Deigo said in a breathy whisper as he leaned over her, "if you get my drift."

Jolene was still hard but she wasn't touching herself. "Yup, that explains why you have a pregnant girlfriend waiting for you back in Texas- the perfect life for the perfect soldier."

"Something like that." Diego stroked his fingers down her chest. He could feel the curve of her ribs, meeting her hips. "lay back." He got off the bed and positioned himself with one hand on her cock, giving it a tender squeeze. His fingers lubed with sweat, he worked her shaft, down to her balls; every part of her was so perfectly hairless, just begging to be touched. Diego placed his lips to her nipple, licking and kissing as he jerked her off, playing her body like the most beautiful instrument.

Jolene was moaning.

Diego wanted so badly to feel her body as writing with orgasm. "spread your legs." He licked two fingers and started to massage her asshole. He would be gentle, going just deep enough to find her pleasure spot and work it until he could feel the precum. "Let me make you feel good."

Jolene's voice was trembling, it was clear she didn't want to cry out. or maybe she just wanted to make him work for it.

Diego could feel her body tense- all the positive motivation he needed to continue. "That's my good girl, I want you to come nice and hard- just let yourself go."

Jolene's back arched as her chest heaved. She went limp, melting into his loving embrace. She turned to him and offered a sweet, gentle kiss. "How long do you have the room for?"

"As long as we want," Deigo replied confidently. In truth, he only had it for that day.

The lovers fell asleep in each other's arms. They awoke the next morning to the typical but loud ringtone of Diego's cell phone. As a computer tech, he was on call, even on this 'vacation.' "Fuck, I gotta get to the base."

"Oh? I thought you were on vacation?"

"Paid leave," Diego said with a groan. "The price of a free trip to the big island."

"Can I see you again?" Jolene asked meekly like it was costing her to admit she wanted to stay in touch. "How long are you in town?"

Deigo admitted the unfortunate truth. "I leave next week, heading back to Texas."

"Oh," Jolene replied, disappointed. She looked at her hands, possibly contemplating getting dressed, then back at Diego.

He was smiling his same Cheshire-cat smile. "Can I get your number?"

"Really?"

"Yeah, Chicha," Diego said as he took a seat on the bed. "We can hang out, have a little fun," he moved in for a kiss, "and next time I'm in Hawaii I'll drop you a line- how does that sound?" Diego stroked the bottom of her chin, raising her face to look into his eyes.

Jolene smiled back at him. "Sounds good, Vato."