Beginning Anew

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

"A-already?" Marcus stammered.

"Marcus, darling, I've been wanting this for so long..." Natalie cooed softly, and gently grabbed her nervous partner around the back of his head, pulling him closer, putting her forehead against his and looked right into his doe-eyes. "I need thisnow. Just looking at you makes me feel like I'm about to blow... That's why I want you to bend over... So I canfill. Your. Ass. Up."

Marcus practically melted right there, from her words alone. "Okay..." he mumbled.

Natalie smirked. "Good. Now get to it!" She gave him a smack on his ass, prodding him to get into position as quickly as possible, while she turned her attention to what she had hidden behind one of the rocks that adorned the edge of the pool: A bottle of lube. She popped it open, and with shaky, eager hands she squeezed out a big dollop onto her raging hard-on. Before spreading it out, she used her free hand to yank Marcus' swimming trunks down in one swell swoop where he stood, bent over with his hands against the glass tile-covered concrete table.

With his only piece of clothing now being afloat where the water surface stopped at his knees, Marcus whimpered in embarrassment. However, the feeling of having a cold, sticky fluid dropped into his asscrack quickly silenced him. A shiver went up his spine as he slowly turned his head to see Natalie standing there, her dick glistening with lube, while she continued to squeeze out a few more thick wads of it onto him.

After covering the insides of his buttcheeks in a thick layer of lube, Natalie dropped the bottle into the water. "Look at this fucking ass of yours..." she said with a flushed, satisfied grin on her face, spreading his cheeks apart. "God, I've wanted to do this for so long... To see your tiny little body writhe in pleasure as I stretch this hole of yours..." As a sort of appetizer, she stuck her middle finger straight into Marcus' little hole, feeling it immediately tense up around her finger.

"Mmm, yes..." he moaned in response. Even though it was just her finger, it nonetheless made him writhe in pleasure, making Natalie's comment about what to come ring true.

"Save those moans of yours, Marcus..." Natalie said and pulled out her finger. "You're gonna be needing them forthis..."

Marcus turned his head back and was met with a view he would never forget. There she stood, his goddess of a neighbour, looking at him with a pure desire to turn him into her little fucktoy. Her perfect teeth showed off in a warm smile, her reddened, freckled cheeks, and the long, dark waves of her hair were all practically beaming along with the rest of her pale flesh in the hot sun. Not to mention the fact that her bikini now being completely discarded into the water meant that he finally got to see her soft, perky tits and pink nipples standing erect in lust.

What Natalie had been referring to however, was that which he couldn't see, but feel. Namely her stiff cock rubbing against his asshole, the slippery surface causing her every up and down motion to massage the inner lining of his anus. Though whether or not she was just teasing or actively trying to gain entry was unclear... but only for a split second.

Without another word her playfulness abruptly ended, and thus her impatience finally shined through as she grabbed Marcus by his hips in an iron grip. This was immediately followed by one long, steady thrust against his warmed up butthole that no longer tried to resist her in the slightest. She gritted her teeth as she felt his warmth encase her raging cock, but she didn't let any of the immediate pleasure stop her from pushing further, instead letting it slowly fill up his ass, inch by inch.

"Oh,fuck," she growled, almost going cross-eyed with pleasure, her cock now covered to the hilt in Marcus' soft boy-flesh. With her hips pressed against his ass, she stopped in place, taking a quick breather and checking up on Marcus, who hadn't made a single sound since the start. "Hey... You okay? Does it hurt?"

Slow, controlled breaths were the only thing Marcus could focus on as he stood there knee deep in the water, his legs almost giving out from the surges of pleasure pulsating from his asshole throughout the rest of him. His upper body was hardly any better off, completely limp and slumped over the table as his weak fingers barely held on to its edges. It was as if his body had instantly been drained of the energy to resist and had accepted Natalie as its perfect match, despite the severe pain that was proving how incompatible their anatomies actually were.

"Marcus...?"

Finally, he managed to gather the strength to turn his head back to her. "Don't worry about me..." he panted, looking like he was on the verge of passing out. "Fuck me, Natalie... As hard as you want to..."

Within a second, the worried look on Natalie's face shifted back to the same old unwavering, confident one. "That's the spirit, Marcus," she said in a sultry tone. Immediately taking him up on his words, she didn't give him any chance of getting ready for her hips abruptly swinging back and forth with nigh ten times the speed and ferocity, now audibly slapping against his soft ass. The squeal he let out as she once again waited with her cock fully inserted was music to her ears, and as soon as he had gone quiet, she delivered yet another identical thrust. Then another... then another...

Some part of Marcus knew that they shouldn't be having sex outside in the first place, let alone with the noises coming out of his mouth as his ass was getting pounded with increasingly powerful thrusts. But he didn't care if any neighbours could hear. There was quite the distance between the houses anyway, so it wasn't exactly a big risk, but no way in hell was he going to hold back his moans.

"My god, Marcus," Natalie groaned between her teeth, already jackhammering the poor boy. "Your ass is fucking perfect... Everything I ever dreamed of..."

"H-harder, please..." was all Marcus managed in response. Natalie's mere words seemed to be enough to make him melt around her hard shaft, to the point where the pain that she was inflicting on him seemed almost negligible. But even with that said, regardless of how much praise his ass got, her throbbing, fat cock was definitely the star of the show.

Natalie chuckled. "Harder, huh...? You're a natural little slut aren't you?" She accentuated her words by swinging her hand through the air, slapping Marcus' buttcheek hard enough to ellicit a loud squeal from him.

"... Only for you, Natalie..." Marcus panted, drooling out of his smiling mouth.

That right there was the best possible thing that could have come out of his mouth. In a millisecond, Natalie went from calm and collected, albeit burning with lust, to lightheaded to the point of almost fainting. Her eyes rolled back into her head and her hips suddenly thrusted forward with even greater force at the prospect that Marcus had already accepted his destiny as her boytoy.

With a thrust so hard that it practically sent ripples through Marcus' entire body, Natalie suddenly stopped, her cock completely embedded within him. Before he even had the chance to glance back to see what was going on, he suddenly had her arms locked around his thighs, and just like that, she began turning him around where he lay, slowly flipping him over on his back with her cock still filling up his rectum. He gasped as his body twisted around it, a completely alien feeling washing over him, but a pleasurable one nonetheless. It seemed like a move that could quite easily cause pain or at the very least discomfort to Natalie, but once Marcus had been turned around and felt his back against the concrete table, the look on her face was still mad with nothing but lust.

"Wow... I... I didn't even know that was possib-..." he said, getting cut off by the gorgeous brunette's lips crashing down on his. They shared their most passionate kiss yet, even though it was completely dominated by Natalie.

After a while she pulled back, but just barely, remaining bent down a mere inch above Marcus' face with several strings of spit connecting them, her long, brown hair hanging around his head, walling him in. "This is only the beginning, Marcus. I'll show youmany things you didn't know were possible... Like when I fill your sexy little ass up with the biggest load of hot cum you can imagine..."

Suddenly, the thought of getting creampied seemed like the sexiest thing ever, despite it being the first time it crossed Marcus' mind. "Well, you know..." he began, biting his lip. "I can imagine quite a lot..."

"Double it," Natalie said confidently, her hips drawing back again. Without warning, she immediately returned to her powerful fucking, this time rocking her hips in a circular motion that almost seemed to lift the tiny boy's butt off the concrete table with each thrust.

"Mmm, fuck..." Marcus moaned. The sudden shift in movement brought him a whole new world of pleasure, instantly making his sudden cockiness fade. Now that she had him in the optimal position, the way that the tip of her cock speared his prostate with even greater force than before quickly reduced him to a limp, drooling mess, his limbs and neck draped over the edge of the table and into the warm water that surrounded them.

Then, almost as if shocked with electricity, his body tensed up again, a gasp escaping his mouth. He looked down to see Natalie staring up at him, her lips and tongue going to town his right nipple while her fingers twisted and pulled on his left one. All this while still having his ass plowed without pause, albeit in a gentler manner now.

One would have thought that having a fat girl-cock up their ass would make any other form of stimuli redundant, but Marcus' body practically started to boil over with ecstacy. With three parts of his body stimulated instead of one, it wasn't an exaggeration to say that the pleasure increased threefold as a result. And as reflected by his suddenly erratic moaning, it didn't take much more to bring him to climax.

"Natalie, I'm gonna cum..." he whined, his legs looped around his lover's lower back, and his fingers grasping the edge of the table in an iron grip.

Natalie detached her lips from his nipple and stood up straight, wanting to have the perfect view of Marcus orgasming. And judging from how gorgeous the view was already, there was no doubt that it would send her over the edge as well. Truly, the only thing that could make the gorgeous boy any hotter would be if he were covered in cum...

With her focus shifted away from his nipples, she more than made up for it by grabbing his twitching little dick and giving it a tug, instantly giving him the final push. Though thin and transparent, his seed nevertheless came out with rather impressive force, shooting out across his belly and chest in little ropes of boy-cum.

"Oh, shit..." he moaned, his balls and prostate emptying themselves as Natalie's static but throbbing cock stretched his asshole.

Just like she had foreseen, this was the finish line for her. With a near psychotic grin on her face and drool leaking down her chin, she gazed over the smooth, tan skin of her lover-boy covered in a criss-cross pattern of cum... And simultaneously having said boy's tight asshole clamping down harder than ever on her cock became a far too stimulating experience to keep her orgasm back.

"Ngh, fuck... Here, take what was promised!" With one last devastating back and forth swing of her hips and her arms pulling Marcus' thighs towards herself, she shoved her thick, pulsating cock in a final time. She could tell the second her big, low-hanging balls tightened that this was going to be a big one; one that represented the pent up sexual frustration from her long time of nothing but silent admiration for her darling Marcus.

The hot rays of the sun were nothing compared to the burning sensation taking place in her core, as if her body was trying to force out her massive load of cum out at once. Letting out a muffled moan and biting her lower lip so hard she nearly drew blood, her cock erupted within her lover's tight asshole, immediately splattering it with an amount that made her aforementioned sensation seem reasonable... But in reality, it was merely the result of one of many pulses of hot semen. She unloaded rope after rope of cum, each one as big as the last, to the point where some of it forced its way out of their tight enclosure and splattered into the pool.

Already spent by his own orgasm, Marcus simply lay there with a look of bliss on his face, his eyes meeting Natalie's as she continued to fill him up. The thick mass of searing cum sloshing inside his guts was nothing but heavenly, but that look on her face... The lip bite, the sweat coating her lightly freckled skin, her squinting eyes glistening in the sun... Nothing on the entire planet could ever match such a beautiful sight.

"Oh my god..." Natalie panted, clenching her pelvic muscles to squeeze out the last trickle of cum. "You fucking milked me dry... Jesus Christ..."

Marcus giggled. "I could say the same about you," he said. "I've never came so hard in my life."

Merely smiling back at him for a few seconds of silence, Natalie allowed the two of them to fully regain their breaths. Then she bent forward, cupping Marcus' cheeks and giving him a quick, yet passionate french kiss. She could tell that the boy was exhausted, but even so, he seemed more than eager to keep showing his rapidly developing love for her.

After pulling away from him and standing upright, Natalie cast her glance down at where her deflating cock was slowly being pushed back out of Marcus' deflowered hole. Drawing her hips back, her cock was practically ejected by the considerable pressure from the fat load of cum she had dumped inside him. And just like they both had expected, the resulting gush of spunk that escaped with a loud, nastyslurp was nothing short of outrageous, as were the splashes it caused as it hit the water.

Natalie looked back at Marcus. "Looks like I kept my promise, huh?"

"Ten times over," he said, his eyes traveling down to her flaccid, cum-stained cock, its tip still dripping cum into the pool. To think that it was that big without even being hard...

His awe was not lost on Natalie, who proceeded to grab her womanhood by the base and hypnotically swing it from side to side. "You wanna try using your mouth next?"

Hardly even listening to her, Marcus was already running his wet tongue over his lips...

-----

Five days later

With plenty of sunscreen protecting her pale body and a pair of sunglasses over her emerald eyes, Natalie's lounger was like heaven in the blazing heat. She rested the back of her head against the soft padding, her dark-brown hair draped to the side along her body, making sure that it stayed out of the way for her nude, perky tits to allow them to gain equally as much of what little amount of tan she was willing to give herself. She had even gone through the trouble of mixing a piña colada to enjoy in the sun. But just as she reached out to grab it, her phone rang.

She gave the display an irritated glance, but despite not recognizing the number, she chose to pick up. "Hello?... Oh, hey! I didn't realize it was you!... Oh, I see, I see. So, how are you enjoying yourselves?... Aww, that's great to hear... Yes, he's being avery good boy! A little tense in the beginning, but heloosened up quickly enough... Hmm, I'd say so. Why do you ask?... Really? For how long?... Oh? Well, I'll have to ask him what he thinks... Alright, I'll call you back. Bye!"

A wide grin spread out on her face as she put her phone back on the porch. "Good news," she said, pulling down her sunglasses and tilting her face down. "Looks like your parents want to extend their vacation another three weeks. They wanted me to ask you if you were okay with that... Although I think I already know your answer..."

With a pillow between his knees and the porch, Marcus remained in place in front of the lounger, happy over the news he had just received but refusing to let it affect his task. His lungs were burning, his face had turned red, and his body was practically convulsing as it begged for a break. But his head didn't stop moving for a second; it just continued to slowly press on with Natalie's thick cock impaling his throat.

After what seemed like another whole minute he decided to come back for air and proper blood flow to his cock-obsessed brain. "That... sounds great..." he panted, his lips and chin covered in drool, as was the gorgeous, twitching shaft in front of him.

"I'll let them know," Natalie purred, petting his cheek with her thumb. "You wanna take a break?"

Marcus shook his head. "No... Not yet. I'm so close."

Natalie giggled softly at his cute determination. It was true; he was close. Less than an inch of her cock remained to be spit-shined, which was a truly remarkable progress in what little time he had practiced since their first time together. And if he could learn to deepthroat her in just five days, the possibilities for their blossoming sex-life were practically endless...

"Well then, be my guest," she said contentedly. Leaning her head back against the lounger once again, she put her sunglasses back on with a smile on her face, her hard cock almost immediately being worshipped anew. She was already going over the list of things she had planned for the two of them over the coming weeks. Things ranging from romantic to downright nasty, some of which might very well stand to change the very essence of Marcus as a person, to the point where his parents might not recognize him anymore. With that said, there was no way her relationship with him was going to end nor be kept a secret once they came home... and she couldn't care less about their opinion on it.

As for Marcus, he hadn't even begun to consider how to break the news to his mother and father. Truth be told, they hadn't even crossed his mind at all since his new,big discovery, and when they did, his new life would surely be set in stone already.

After a long time of the two of them living in frustration, they could finally agree on one thing...

Life was good.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
37 Comments
1Martiniman1Martiniman28 days ago

This story is everything you can want from a trans love story…it’s erotic, well written, great characters and just an overall good premise and story. A must read!

FlipaBaka69FlipaBaka69about 2 months ago

Definitely one of the best stories on this site! It was a great ride, filled with a bit of emotion, character depth, and pretty hot at the end! My only critique is that there aren't any more chapters to read, especially since you left the ending so tantalizingly open to showing us what they'll be up to the next couple of weeks. Please continue writing this story! (If you want to)

AnonymousAnonymous2 months ago

A super delicious & erotic story. I would love to be Marcus. Wow! That would be so much fun. While reading the story I was thinking his mom knew Natalie was a trans & also knew her son was gay/straight. She & Natalie planned this time as a kind of sexual basic training for Marcus in order for him to realize & accept who he is.

Please write a ch2 of this hot story.

AnonymousAnonymous4 months ago

This was awesome

JackiemichelleJackiemichelle10 months ago

Couldn't stop reading. Wishing she was my neighbor. Please finish the story and take me where you want it to go. Please finish

Show More
Share this Story

Similar Stories

In Time for Summer A boy gets seduced by his "lesbian", packing roommate.in Transgender & Crossdressers
Futa House A boy unwittingly discovers a gold mine of girlcock.in Transgender & Crossdressers
My New Trainer Workouts will never be quite the same.in Transgender & Crossdressers
The Big Mature Shemale Next Door Little guy is fed cum and seduced.in Transgender & Crossdressers
Southern Hospitality Milfy seductress does all she can to score the boy next door.in Transgender & Crossdressers
More Stories