Anyone turned off by crossdressing and flouncy little gayboys should give this story a pass. But if that's your cup of tea then read on and, hopefully, enjoy! Oh and for those wondering I'll be releasing the other stories from the suggestion post next week so check back in then!
“Oh fuck, oh fuck, oh fuck, ohhhhhhh FUUUUUCK I'M GONNA CUM!”
Throwing her head back and squealing until her lungs were empty and her throat was hoarse Ana Lucia was all but completely overwhelmed by the pleasure crashing down on her. Almost violently grinding her hips and slamming herself down onto her boyfriend she moved like a feral animal. More frantically than even the wildest pornstars. Shudders rippled through every last inch of hr plump, curvaceous figure as tangles of curly black hair completely hid her soft round face. Beads of sweat rolled down her flushed, soft brown skin while messy flecks of warmth constantly splashed across them both as her frantic movements grew ever more feverish. And all the while Deion rubbed her clit and pushed back against her frenzied movements without even trying.
No matter how wild she might've been her gorgeously experienced man didn't have any trouble matching her desperation. Not to mention pushing her even further over the edge. Everything he did turned an already incredible taste of ecstasy into something utterly and completely devastating. The kind of full body, mind shattering ecstasy that defied all reason.
And she continued to bask in the madness for what felt like minutes on end. Even after her own body failed her and she slumped against his chest to desperately claw at his back and hold him close he didn't stop. She wasn't even sure how he still managed to ruin her but she didn't care. Between his fat cock and his soft, slender arms around her body she was in heaven. But alongside his constant teasing of her clit Ana Lucia was positively losing her mind. Hell even the slow comedown from her ecstasy as Deion gradually relented was beyond words.
“That was... amazing...” She panted, still sprawled across him and all but smothering him beneath her as she lay there panting, “So... fucking... good...”
“Yeah, it really was...”
Though she loved the warmth of his breath against her skin and would never, ever get tired of feeling his fingers brushing aside her hair Ana Lucia was too distracted to revel in either. Too distracted by his still unimaginably hard cock throbbing away inside her, “You didn't finish.”
What used to be a question was simple a resigned statement as she pushed herself upright to look at him, “No.” He replied. “But I still enjoyed it a lot!”
“I'm glad to hear it.” Not so long ago she would've been working herself into knots worrying about why he hadn't finished. About what she'd done wrong. But they both knew she didn't have anything to do with his almost complete inability to cum. “I still feel a little guilty though...”
Ana Lucia lifter herself off his cock and laid down beside her boyfriend, his arm immediately wrapping around her shoulders as he said, “Why? It's not your fault.”
“I know... but I guess part of me was kind of hoping I'd be able to do it eventually.”
“Yeah I think part of me was hoping the same thing.” He admitted with a laugh, “But I'm not gonna complain! I'm not sure I have any right to, I'm still convinced it's my fault somehow.”
They both shared a little laugh as they simultaneously thought about the life he'd led before she met him. Although her thoughts rather quickly returned to the present as she asked, “Do you remember that conversation we had on your birthday? When we were sharing our crazy fantasies?”
“Yeah?”
Lifting her head to rest her chin on his smooth chest Ana Lucia bit her lower lip and said, “Well I've been thinking about that whole conversation a lot...”
Deion laughed and shook his head, completely unsurprised by that 'revelation'. “So which one do you want to try now? I'm not sure I'm ready to go back to a sex club but I wouldn't mind trying out some of that other stuff you wanted.”
“Oh this wouldn't involve me at all.” Ana Lucia replied, “This one's all you... and it actually works out kind of perfectly when you really think about it...”
“Well don't keep me in suspense!” He laughed, “What's this big idea?”
Sliding out of his brand new sports car and adjusting his finely tailored suit with his free hand Lionel heaved a dramatic sigh as he shook his head, tempted to hang up on his sister altogether and spare himself another circular conversation, “You know I'm actually starting to regret giving you that money.” He remarked, “If I'd known it was going to dominate half the conversations we had I would've let you get kicked out of your apartment!”
“Oh shut up!” Ana Lucia laughed, “I'm not calling about that! Well, not in the way you think!”
“Really? You're not gonna talk my ear off about some new harebrained way to pay me back?” He asked, “I won't have to suffer through another home cooked meal?”
“You love my cooking!”
“I love our abuela's cooking. Not your attempts at recreating her cooking.”
Grinning as he emerged from his detached garage and walked down the winding path to his extravagant home Lionel could all but see the look on his sister's face in the momentary silence that followed his remark. And he could hear it in her voice when she said, “Are you gonna listen or what?”
“Fine. But I'm hanging up as soon as you start repeating yourself.”
“Well lucky for me I'm not gonna repeat myself! Because I thought of the perfect way to pay you back and—”
“I'm hanging up now.”
“—AND help Deion out too!” She finished.
Pausing midway through entering the code to his front door and nearly triggering the security Lionel fumbled his way through the rest of the code as he asked, “Deion? Why would Deion being involved in any of this?”
Ana Lucia giggled at him but didn't respond. Not until he was actually inside his house and walking through the entryway as a familiar yet shocking voice said, “Hey handsome... long time no see!”
Nearly dropping his phone as he jumped out of his skin Lionel staggered backwards into the nearest wall, his head whipping around until he finally spotted the 'stranger' standing in his living room wearing a smile and very little else, “You can thank me later!” Ana Lucia remarked.
She hung up the phone before Lionel could say anything but he was far too busy staring at Deion to respond to her anyways. Dressed in the most lewd, provocative outfit Lionel had ever seen, at least in person, he didn't look anything like the man he'd met dozens of times over the last year. Long, not quite sheer knee socks covered most of his unexpectedly shapely legs, teasingly drawing his eyes higher and higher as he stared in disbelief. Only for him to immediately look away the moment he saw the unmistakable bulge of cock straining against lacy panties so skimpy they hardly covered anything at all. Though his underwear certainly matched the belt masquerading as a plaid miniskirt around his genuinely girlish waist. To say nothing of the loosely unbuttoned blouse showing off his smooth chest and contrasting so well with his dark brown skin. Much like the bright pink wig accentuating his feminine face and the makeup he'd carefully applied to draw out every womanly angle.
“What the hell is going on?!” He demanded, doing his best not to betray how hard his heart was beating at the sight of such an exquisitely sexy femboy. “What are you doing here? Why are you dressed like that? Why in the hell did Ana Lucia send you here?”
Slowly biting his lower lip and sauntering closer Deion moved with a cocksure strut like a model working the catwalk as he asked, “Isn't it obvious?”
“Nothing about this situation is obvious.” Lionel replied, his eyes instinctively roaming the soft curves and beautifully womanly figure of his sister's boyfriend. “Has he always been so... hot?” He thought with a nervously inhale, “He hasn't... has he?”
“Ana :Lucia must not have told you then... before she and I met I used to spend a lot of time dressed up like this. A lot of time taking pictures and making videos of myself on the internet.”
“Deion I don't—”
“Jasmine,” He purred, “Call me Jasmine now.”
They were barely two feet apart from each other as Jasmine spoke those words and Lionel couldn't help but catch the faint scent of something sweet and tantalizing on the air. “All right, Jasmine... I don't know what you and my sister were thinking but I'm not—”
“We both know I'm exactly your type.” Jasmine giggled. “You might not want to admit it bit Ana Lucia knew it and now I know it too...”
Finally close enough to touch each other Jasmine smiled up at Lionel with a look that could melt an iceberg. And of course Lionel could only stare back at him with a mixture of amazement and disbelief as he tried to think of something to say. Anything. It didn't even have to be particularly coherent or worthwhile. But his voice was completely stuck in his throat and he couldn't figure out how to move even one of his limbs.
Not until Jasmine suddenly produced a little bottle of lube from seemingly nowhere and said, “I think we've wasted enough time.”
“You can't be ser—”
His words were cut short by a groan as Jasmine teasingly cupped his painfully hard cock, groping him through his slacks for just a moment. Just long enough to completely silence anything he might've tried to say. And a moment after that he was unzipping his pants and slipping a hand into his underwear, both of them moaning as his unimaginably soft fingers closed around Lionel's cock. But while one of them was left almost totally frozen the other didn't have the slightest issue freeing his lover's fat prick, and even his massive balls, from his underwear. Nor did he hesitate to absolutely drench his entire length in a thick coating of lube soon after.
“You don't have to be gentle...” He moaned, stroking Lionel's cock and lathering it in a gooey layer of lubrication, “And you don't have to hold back...” Jasmine poured a little more onto his shaft and teased him just a little bit longer, “Just fuck me... just fill my tight little ass with cum!”
Every word out of those beautifully plump lips made Lionel's head spin. And yet by the time Jasmine was finished, his fingers slowly falling away after one last teasing stroke, his body reacted without any help from his mind. One moment he was staring down at the gorgeously slutty femboy standing so boldly in front of him, the next he was pinning Jasmine against the wall. With one hand flat against his back and the other tearing at his tiny little thong he removed anything that might get in the way of his cock. And the sight of those plump, quivering cheeks just waiting to be split by his prick was all the encouragement he needed. Though hearing Jasmine's wild, girlish moans as he looked back at him with a giddy smile certainly didn't hurt. Even if he barely noticed as he pressed the head of his cock against the tightly clenched, amazingly puffy ring hidden between those bountiful curves.
Not so much hesitating and readying himself Lionel took all of a second to widen his stance and get into the best position possible. But even that seemed like an eternity to Jasmine. An eternity of breathless anticipation and utter desperation as he waited for his treat. But it all came crashing down in the sweetest way imaginable when eight inches of deliciously thick cock slammed into his ass with a single stroke. Every last centimeter plunged into him in a single burst of toe curling ecstasy, the fat balls he couldn't wait to drain smacking against his skin with an almost thunderous slap. One that was completely drowned out by Jasmine's breathless squeal and Lionel's deep, satisfied groan. Both of them were instantly and completely overwhelmed by the other. Immediately left drowning in the sheer, unbridled pleasure that was their illicit little tryst. All the air was pushed out of Jasmine's lungs in the blink of an eye only for him to breathlessly suck in as much as he could when his lover pulled out just as ferociously as he'd thrusted forward.
But he didn't get to enjoy that breath for long as Lionel's cock split him open all over again. As it stretched open his greedily quivering inner walls while the rest of his body pressed against him and his warm breath buffeted Jasmine's cheek, “Are you wearing a chastity cage?”
“Of course I am Daddy!” He whimpered.
Lionel's cock throbbed even harder inside Jasmine's ass and his voice was almost guttural as he simply replied, “Fuck!”
That single word hung in the air for all of a heartbeat before Lionel immediately launched into an absolute frenzy. Moving faster and harder than Jasmine could've imagined he pulled out and plunged back inside him in a toe curling barrage of pure strength. Fucking less like a human and more like some wild animal finally unleashed in the throes of mating season he absolutely pounded Jasmine's tight little asshole. Utterly destroyed his puffy little ring and turned him inside out with every wild stroke, almost instantly pushing him to the brink of sanity after only a few moments. It'd been so long since Jasmine took a real cock and even longer since he took anything as thick as the cock slamming into him now and he was really feeling that time! And yet there wasn't any pain or agony as he was slammed against the wall and fucked like a cheap, back alley hooker.
Only the tiniest flashes of discomfort amidst crashing waves of pure ecstasy. Between the simple joy of having a fat cock in his ass again, the pure depravity of it being his girlfriend's brother, and the way Lionel absolutely jackhammered his tender prostate Jasmine was already on cloud nine. Within a minute of the madness starting he was gasping and squealing like a pornstar putting on the most over the top show of their life. His eyes were rolling back in his head and his fingers were clawing at the wall he was being slammed into over and over and over again. But there was no insincerity in his moans and certainly no faking his ecstasy. Every single reaction was as genuine as he could be, his long dormant inner slut finally reawakening as Lionel absolutely ruined his slutty hole.
And because simply being fucked silly for minutes on end wasn't enough of a treat he could already feel Lionel's cock twitching and throbbing with an all too familiar need. Jasmine could feel his lover's balls tightening as they slapped against him and hear the feral desperation in his moans. Anyone else might've been disappointed by how quickly he was approaching his limit but Jasmine had never felt so elated in his life. After years upon years without that unbelievable gratification he was finally about to enjoy the ecstasy Ana Lucia hadn't been able to give him.
Though only after several ferocious minutes of nonstop pounding. After something like five unbroken minutes raw, relentless dicking. Lionel didn't last any longer than that and it seemed like he couldn't last any longer than that. Much to Jasmine's utter delight and very, very noisy appreciation. So noisy in fact he almost didn't hear the three sweetest words in the English language when Lionel spoke.
“I'm gonna cum!”
“Inside me!” Jasmine howled, “Cum inside me! Cum inside me! Cum inside meeeeeeeeeeeeeeeeee!”
Whether his breathless squeals pushed Lionel over the edge or simply punctuated his ball slapping frenzy Jasmine didn't know. And he honestly didn't care. As soon as he felt his lover's cock slam into his ass one last time, pressing hard against his prostate, everything else in the world simply disappeared from his mind. He barely even had time to suck in a desperate little breath before streaks of searing hot cum exploded into his depths. Before thick, gooey loads basted his tender g-spot and instantly pushed him over the edge for the first time in so unimaginably long.
Suddenly both of them were grunting like wild, rutting beasts as downright violent shudders ripped through Jasmine's body. Fountains of thick, pent up cum squirted from his caged cock to spray all over the wall, floor, and his trembling inner thighs as years of anguish were finally unleashed. Lionel's ecstasy might've come in creamy spurts and massive loads but Jasmine's was almost a single, continuous stream as he screamed in ecstasy until his voice failed him. It sprayed and leaked out of his cock in an endless flow enhanced only by the waves of shuddering ecstasy tearing through his body again and again. All thanks to the deluge of fresh cum basting his inner walls and, most importantly of all, soaking his g-spot in a gooey layer of warmth.
Long after Lionel had finished pumping Jasmine full of cum Jasmine continued to shudder and squirt in fits of ecstasy. For what felt like minutes on end spunk dribbled out of his cock at the very least and erupted out of it at the very most. All the while he was left convulsing and shuddering so hard he would've collapsed if not for Lionel's hands on his waist.
“Holy shit...” He panted, leaning back to see the absolute mess Jasmine had and was continuing to make, “I've never seen anyone cum like that!”
“I can't... I can't cum... unless someone else... cums inside me... unless they cum all over... my g-spot...” Jasmine panted, “And it's been... a very... very... long time...”
Lionel shivered just the tiniest bit at those words and his cock stiffened. Jasmine moaned at the stimulation and looked back at the man behind him, already on the same wavelength before Lionel even spoke, “Sounds like you're pretty backed up then...” He grinned, “How about we see if I can help you out a few more times?”
“As long as you don't mind the mess I'm all yours handsome!” He moaned.
“I like the sound of that!”