Chapter 5
Ashland just sat there looking at the man.
“What are you waiting for babe?” He reached out for Ashland’s wrist and guided him to the back of the vehicle. Ashland took a seat at the end of the bench and just blankly starred at him, as if he was a deer in the headlights. “Ok fine. I get it,” he said, as he reached into his pocket. He pulled out sixty dollars and held it out in the air at Ashland. “Ashley!” Ashland just stared at it, as if he had never seen money before in his life. “Fuck! Okay, okay!” He reached back into his pocket and produced five twenties this time. “Enough?”
Not wanting to expose himself, Ashland took the money and put it in his purse. As he looked back up, there was John at his face—planting another kiss on his lips. Ashland took the man’s embrace—allowing John to part Ashland’s lips and slide his tongue in Ashland’s mouth. He kissed the man back, and as he did, he felt the man’s hand touch his thigh then slowly move up his leg. Ashland reached out and grabbed the man’s wrist just before his hand slid up the skirt of Ashland’s dress. Ashland used his other hand against John’s shoulder to push him away, causing him to release his grip on Ashland’s lips. John fell back into the seat and wiped the saliva from his mouth. John tugged on Ashland’s wrist and pulled Ashland over to him. “Now it is time for my lap dance,” he said.
He tugged Ashland over—grabbing Ashland’s thigh and pulling Ashland’s leg over his body; he was straddling John’s legs now. Spreading his legs made his tiny cock unbury itself from between his thighs, and his separated balls, which were flagging either side of his small shaft, pulled themselves together. ‘Shit,’ he thought—suddenly feeling exposed. The breeze of the night swept through Ashland’s thighs, wicking away the buildup of heat from within. The cooling effect and the stimulants in his body caused his balls to tighten up like never before. In fact, he could almost feel them retreat inside his body, and his cock shriveled in his panties.
John pulled Ashland’s knees up to his hips—situating Ashland over his pelvis. Ashland sat back on the man’s thighs instinctively. John moved his hands to Ashland’s ass and squeezed his cheeks tight. Ashland would be lying if he said it didn’t feel good. “Umm, that’s it baby,” he moaned. “You feel so good.”
For a moment, Ashland realized the predicament he had gotten himself into. ‘What the fuck am I doing here,’ he asked himself? ‘How am I going to get out of this situation?’ Ashland realized he had all the information he needed. This John was one of Ashley’s Jons—clearly—and Ashley was obviously a stripper and a whore. That was where she got her new income. ‘What else do I need to know? She seemed really happy for once in her life, but was it the drugs or the money?’ Ashland was still undecided, but then John found Ashland’s mouth again and began to kiss him.
Ashland kissed him back, and as he did, he felt John’s hands sliding across his skin—across the top of his outer thighs then under his dress. John moved his large hands—warm with desire—to Ashland’s bare ass, where he gripped the flesh. Maybe it was the kissing; maybe it was his hands on his ass; maybe it was just time, but Ashland felt the heat from the ecstasy building in his body once more. He felt the wave build, as his body began rolling again. This caused Ashland to arch his back and head, which led John to move his mouth from Ashland’s young lips to his neck. John ran his mouth along Ashland’s neck—circling his tongue and hot breath against his flesh.
Ashland was fully engulfed in the sensations, as his body rolled from the ecstasy. He pulled John’s head into his neck—uncontrollably moaning—while he spread his flexible knees wide on the seat, which allowed John’s firm grip to pull Ashland’s ass into his pelvis. As he did, Ashland’s hot taint made contact with John’s large, swollen cock through John’s slacks; he had Ashland’s minidress up around his waste now—exposing Ashland’s ass to the darkness of his SUV, as his hands continue to squeeze and knead Ashland’s booty.
Ashland was initially shocked at the sensation of another man’s hard cock pressed to such an intimate and vulnerable area of his body, but admittedly, in the moment, it felt really good. On Molly, almost anything or anyone can feel good, but this was more than that. It felt good to be desired too. It felt good to know he was arousing and pleasing another person just being himself—well, his sister. Ashland never new his dad, so it felt good to feel small in John’s large hands and on John’s large lap. Maybe it was mostly the Molly, but John’s touch felt electrifying, and Ashland was enjoying every moment—careless and sensuously undulating his body against his partner. Ashland had always been curious about larger cocks, as his was especially petite for a man, so when his taint made contact with a large, thick mass in John’s pants, he couldn’t help but feel a bit curious what John was packing—what it was like to own such a cock.
Ashland rotated his hips and pressed his taint harder against John’s cock making John moan. He looked back down at the lust and pleasure in John’s face and smirked. He bit his own lip to hold in the heat of his breath, as he began to contort his hips—stroking his taint against John’s large cock. John’s eyes were closed, his head was arched back on the seat now and his mouth was gaping open, as he basked in the sensation of Ashland rubbing his cock. Ashland could feel John’s cock getting harder; he could feel it swelling thicker in his pants and the heat between them building. Ashland leaned back, as John still gripped his bubble butt. Ashland undulated his hips in long strokes, running his taint from the tip of John’s cock to John’s balls.
“Oh shit,” Ashland moaned quietly under his breath. The waves of pleasure were passing over his body hard now; he was beginning to roll hard—sometimes spasming or gyrating uncontrollably. He was breathing heavy and his body and hips were starting to contort as the waves passed through his body.
‘I suppose he paid for a lap dance, so he should get a lap dance,’ Ashland figured. He quickly flipped himself around and planted his bubble butt right back on John’s hard-on. Instinctively, John spread his knees, and Ashland’s bare ass fell deeper into John’s pelvis.
Ashland could feel the distinct shape of John’s hard cock now beneath the fabric of John’s pants. It was pressed against Ashland’s bare, bubble butt, which was pursed against John’s thighs. Ashland was engulfed in another wave of heat coursing through his body—rolling hard once more. Ashland leaned forward and pressed his ass back against John’s cock, which caused his cheeks to part and allowed John’s shaft to slip between. Ashland began to undulate his body—twerking his ass against John’s cock—stroking the shaft with his movements.
“Oh fuck yea baby. That feels good,” John moaned. John’s hands were initially around Ashland’s small waist—guiding Ashland’s movements, but then they moved to Ashland’s hips the to his sides, which allowed Ashland the opportunity to freely do his sister’s work. Ashland circled his hips—gyrating up and down—then he spread his legs, which caused his ass cheeks to squeeze John’s cock, which enabled him to stroke John’s cock with his ass, as he arched his flexible hips up and down.
John was getting more and more worked up. Even Ashland was getting worked up too and could feel that his cock was hard, which was just peaking up beyond his panties. “Wait, wait, wait,” John said, as he pressed Ashland forward and off his pelvis. Ashland grabbed onto the headrests of the front seat, while squeezing his legs together and bending forward. He looked back at John as John unclasped his belt buckle. Ashland could feel his heart rate quicken and swallowed hard. John unbuttoned and unzipped his pants and worked them off. John’s rock hard cock was more visible now with a clear outline in his briefs. It was at least eight or nine inches and thick. ‘Fuck that shit is big,’ Ashland thought. John pulled Ashland back on his cock, and Ashland continued to give him a lap dance. “Oh fuck yea, that is better,” he moaned. Ashland’s bare, hot ass was sticky, and as he moved, the material of John’s briefs kept getting pulled down. Eventually, the tip of John’s cock was expose, and Ashland could feel the hot, soft head against his cheeks. Ashland was rolling hard—basking in the sensations of their bodies against each other. It didn’t take long before he couldn’t help himself, and he moved his propped hands from John’s thighs to his briefs and tugged at them. John didn’t hesitate when he felt the gesture, and he lifted his hips and slid his briefs down.
“Ohhhh yeaaa,” Ashland moaned, as he felt the raw sensation of John’s smooth, large cock pressed against his bare ass. Ashland’s hot, burning flesh, which was wet from perspiration, began to coat John’s cock, and in no time, the slick shaft worked its way between Ashland’s cheeks. Admittedly, Ashland loved the sensation of John’s cock between his ass. He began gyrating his hips on John’s cock—rubbing his booty against John’s pelvis. The base of his cock was pressed against Ashland’s thin panties, and behind them, Ashland’s taint and sphincter were being rubbed and teased.
“Oh my god Ashley. I’ve never felt you this hot; you’re on fire.” John moaned.
It was true. Maybe it was the Molly, or maybe it was the adventure of doing something so daring—playing the role of a sexy woman sexually pleasing a total stranger. Whatever it was, Ashland was on fire—burning with desire for a man for the first time in his life, ‘but it was normal’, he reasoned. ‘He was a young woman, and young women are suppose to please strong men,’ he said to himself shockingly. Shaking his head in disbelief at his own thoughts, as John was kissing the back of his neck.
‘Where the fuck did that thought come from?’ He could feel some clarity returning, as the waves were subsiding—a moment of sobriety. ‘This does feel amazing, but I’m a guy,’ he thought. ‘I’m not attracted to men, yet I see them naked all the time when I watch porn, and it is no big deal. In fact, I love watching women suck a huge cock; they make it look so delicious. And it is so hot when a hung stud fucks some hot girl too—busting nut all over them—showering them with cum. Oh shit! What if all this porn has made me want cock! What the fuck? This is like some sissy hypno shit or something!’ Ashland’s mind was regurgitating a million deep, seeded thoughts that had been buried in his unconsciousness forever. The opportunity to dress as Ashley was the catalyst that unleashed Pandora’s Box, and there was no going back.
‘But, yeah, what the fuck am I doing to this guy? This poor guy is getting teased like crazy. His poor balls must be blue as fuck—swollen and in pain—full of cum. I guess that is what he paid for like most of these guys at strip clubs. Unless he paid for more…? Oh shit, what if he paid for more?’ Ashland remembered the condoms in Ashley’s purse. He continued the private lap dance, but he was getting nervous. ‘Yes, John’s swollen cock feels amazing between my ass, but probably not in my ass! I don’t think that would feel good at all. I don’t really want to fuck a guy. Do I? Shit! And he is expecting a wet pussy! Shit! How am I going to get out of this? He is going to be pissed. What if things get violent? Fuck! What if he just paid me for sex, and I back out?’ Ashland’s mind was going crazy from the unknown. He needed to act first.