Chapter 7
Tia gripped his ass again, squeezing his round glutes in her hands, then massaging them in circles. She walked her knees forward, taking a position straddling his thighs. She sat for a moment, sinking her ass into his thighs. She came off his legs, barring her weight on her knees again. She leaned forward, bracing her hands on his back and walked her hands slowly up his back. She leaned her torso down, the tips of her nipples were just barely teasing his skin with their presence, as her ass arched in the air. She leaned to his head and whispered in his ear, “I’ll be gentle. Don’t worry.”
He didn’t really know what she meant; he was euphoric and intoxicated in her touch, just a willing participant with whatever she had in store.
She pressed herself up off him and shifted her weight back, walking her hands back down his body, returning to her position above his thighs with her hands back on his glutes. She walked her knees further forward, straddling his hips. She dropped back, lowering her ass to his upper thighs and sitting her weight on him. She gripped his hips, sliding herself forward. As she did, she slowly spread her legs, sliding her soft inner thighs wider than ever before, and she leaned forward. As she did, something was different. Mr Romero could feel something soft and round resting on his his legs. Then he felt a warm rod being pressed then sliding between his ass cheeks. It honestly took him a moment to realize it was a cock; it was Tia’s cock and balls. WTF!
Mr Romero was paralyzed for a moment. He was in a sudden state of shock. His mind was rapidly trying to piece together the situation, trying to recapture an understanding of the events that had transpired. He knew Tia was gorgeous and had breasts—but had a cock! She must be transgender—a ladyboy! The stories of Thailand were true!
While he was locked in paralysis, Tia didn’t change her pace. She had slid her hard cock between his ass cheeks, pinning it there with her fingers. She was lathering her cock with the massage oil and pressing her shaft against his sphincter. She slowly began to press her hips back and forth, sliding her thighs against his easily. She pressed his ass together, fucking his cheeks like they were tits.
His mind was racing. What did he sign himself up for? Maybe this was why the drivers of the Tuk-Tuk were laughing earlier. How was he going to get out of this? Did he even want to get out of this? He had no time for reflection; Tia had already decided for him.
He could sense she was very turned on. She was breathing heavy, and her hips were moving with a sense of lust. She wasn’t big like him. Maybe six to seven inches max and only a little larger than a thumb or a few fingers in girth. He wasn’t scared of her size. He was more in shock than anything. She was gorgeous; there was no doubt about that, and truth be told, she felt amazing, even now. As she worked her cock back and forth, rubbing the rim of his sphincter with her shaft, he began to relax to her, and his body quickly remembered how horny it was, how willing it was to bend itself to her will.
She released her grip on his cheeks, allowing his ass to part, and she pressed the soft head of her cock against the opening of his anus. The tip just slipped in, and she moved it back and forth until his sphincter relaxed. She repositioned herself, and she pressed her cock forward more, and it slid along his sphincter wall, pressing itself up against his inner sphincter. She paused there and began to massage his ass cheeks again. He could feel his inner sphincter tensing, and so could she. She continued to rub his cheeks, easing the tension out of his body. She could feel the flesh easing, giving way to her cock. As it did she gently began to press in subtle motions until her cock finally broke through. When it did, she pressed forward, and her cock slid into his anus.
She held that position for a moment, then grabbed his hips and pulled herself forward, sliding her thighs up his to his glutes, sliding her cock deeper in his ass. Mr Romero grunted a deep moan. “That’s it. Just relax yourself Mr Tony. Tia will give you your Deepest Massage now,” and she did. While gripping his hips, she began to stroke her cock into his asshole, sliding back and forth easily across his oiled, slick flesh. “Mmmmm, fuck yea Mr Tony. Your ass is burning on fire.”
The sensations were completely foreign to Mr Romero, but he was surprisingly enjoying every moment of it. Her cock was so hot and hard, on fire in his ass, yet it was so soft and slick that it felt amazing sliding along the muscles of his sphincter wall. Tia was awakening something new and amazing in him.
As she continued, he began to match her thrusts, pressing his hips back against her firm presses, and opening his hips to her. Her booty was rhythmically squeezing (he could feel this against his thighs), as she pounded her meat into his ass. She leaned forward, bracing herself on his back, positioning herself over his hips, and he arched his hips more. Soon the pace was quickening, and his ass was now smacking against her hips. Clap, clap, clap was the sound, as she began to fuck him harder. Mr Romero was moaning now, willful turning into her sub.
Then she stopped. She was breathing hard, panting and trying to collect her breath. “Mmmmm nice Mr Tony,” she said, as she slowly moved her cock back and forth in his ass.
She leaned forward and laid her body on top of his. She pressed her breasts to his back, her nipples slipped along his slicked up muscles. She lowered the full weight of her body on his, stretched out on top of his frame. She cupped her arms under his shoulders, clutching his upper body, hooking him in a strong grip. She whispered in his ear, “Now, I will massage you deeply Mr Tony.” Then she bit his ear and sucked on his lobe. She was still on her knees; her hips were still floating over his ass. She pressed her hips down hard, mashing his glutes with her hips, and in the process, she plunged her cock deep in his ass. From that position, her cock was deeper than before and aligned with his prostate. It thumped across the sensitive and swollen flesh that was burning hot within his rectum, and as she did, his prostate spasmed causing cum to ooze from his cock.
“Oh fuck,” he moaned. It was clear he enjoyed that thrust.
“Yes Mr Tony,” she said lustfully with a smile. “Just wait until I get going,” and she began to slide her cock back and forth in his anus, grinding her cock against his prostate, massaging him from the inside. “I will release all that tension. Just give yourself to me Mr Tony.” Mr Romero complied with her commands, and he opened his hips to her, arching his ass in her direction. She gripped his shoulders tight and pulled herself hard against his body, never breaking contact, forcing her cock deep within his body, as she thrusted. With each thrust against his prostate, with each milk of that organ, cum oozed from his cock, and the head of his penis seemed to be electrifying with sensitivity. “Yes Mr Tony,” she continued. “Cum for me. Release yourself.”
He was nearing an orgasm, and she could sense it. His body was stiffening, as his hips intuitively arched to their maximum position. His orgasm was on the verge of breaking; he was about to have his first prostate orgasm, and the anticipation and desire was overwhelming. “More Mr Tony?”
“Yes!”
She quickened her thrusts. “Harder?”
“Yes!” He was moaning loud, begging her to bring his orgasm.
She began pounding his ass, slamming her cock against his prostate, shaking his hips with each strike. Smack, smack, smack against his ass. His orgasm was on the brink of coming. The delayed gratification was drawing his orgasm to a height he had never felt. Then it came!
Mr Romero burst in an orgasm, “Ohhh ohhh,” he moaned, as he exploded in an orgasm. His hips released their static arch, and they began to convulse on her cock, forcefully gyrating on her shaft, as his orgasm flooded over his body, making him lose control. Streams of hot cum shot from his cock, shooting between his legs. It kept coming!
“Yessss Mr Tony,” she moaned back, never changing her pace, as she continued to pound his ass, slamming her cock against his spasming prostate. His sphincters were pulsating on her cock, clenching and squeezing her shaft, as each contraction of his orgasm proceeded. The feeling was intense for her, and she couldn’t hold back any longer. She exploded in an orgasm too, “I’m cummming Mr Tony!” Her cock began to pulsate, rhythmically contracting, shooting her hot load in his ass.
He could feel her cock contracting against his spasming sphincters; the sensation was out of this world amazing. Her cum was lubricating his sphincters more, intensifying the sensation of her cock sliding in and out of his ass. “Ohh fucckkk yeaaa,” he moaned, as she continued to unload herself in his rectum. She kept pounding him, digging her hips into his ass with each thrust, pressing herself as deep as she could while unloading her seed.
As their orgasms began to subside, she quickly slowed her pace, as the two settled their weight into the mattress. She laid on his frame with dead weight, seemingly exhausted from her work—her cock, still in his ass. As the two of them caught their breath, she was still, ever so subtly and gently, gliding her cock back and forth in his slippery anus, while basking in the glow and euphoria of their session.
“Mmmm,” she whispered in his ear. “That was good,” giggling. She nibbled on his ear some more before sucking on his lobe. “Was it good for you Mr Tony?”
“Oh yes, my dear. You were amazing.” He never thought he would be telling a ladyboy that she did an amazing job fucking him. He never knew he could cum so hard, or that he would enjoy a cock in his ass either, but this was Thailand—a place of new experiences, and apparently, of the Deepest Massage.