Entry 7: First Experiences [02] *

‘Hmm… Nah, fuck that. It’s high time I lose my virginity. I’ve been waiting 38 years for this very moment. And even if their relationship seems like it’s on the rocks right now, who’s to say Emily and her husband aren’t still sexually active with each other? I don’t plan to take my chances just yet.’

[22:07]

Upon glancing at the timer in the corner of his vision, Samuel decided that he could earn points from cunnilingus in the future sometime- a decision reinforced by the weak excuse that he was almost out of time. He finally put the stray thought to the back of his mind once he’d rationalised to himself why not to do it, before standing up and fumbling to remove his track bottoms.

Samuel could vaguely remember owning a pair of tracksuit bottoms such as the ones he was wearing currently, late into his life. Given the stretchy material, it was able to accommodate his growing waistline much better than a pair of jeans might have. And right now, the young adult couldn’t help but marvel at the efficiency of the trousers that was as easy to take off as it was to put on, perfectly complimenting the process leading up to the point when Samuel would take his first step into adulthood.

The enthusiastic teenager then threw off his cardigan, which he had hurriedly thrown on just before leaving the house. A t-shirt, and boxers- sheathing a modest 5-inch penis- followed suit, leaving the horny male in his birthday suit.

With his newfound nude status, he quickly got back in between the legs of the woman, as though planning to return to the comfort of the womb. But while he was crawling his way back into a comfortable position, the tip of his cock, which swung from side to side because of the forward motion, grazed the soft thigh of his neighbour sending a sudden jolt of pleasure down his spine.

Samuel stiffened as he could feel he was close to bursting with just that one touch. He contracted every muscle in his nether regions just to thwart any premature release, and with the blessings of some unknown deity or other, he just about managed to get through the cramped feeling in his shaft without letting go.

‘That was a close call. I wouldn’t want to cum now just in case it takes too long to charge up again.’

Samuel- blinded by the long recharge times that came with his growing penile insensitivity from jacking off to online images in his past life- thought to himself, unaware that the allure and pheromones of an actual woman would probably be able to get him hard again in no time.

Finally, the young adult reached the point where his cock could slide into the gorgeous wet pussy presented in front of him. He was leaning over her, somewhat struggling to prop himself on his elbows, with her plump thighs strewn across either side of his chubby frame.

Bringing his right arm down to line his cock with her slit as he looked down through the valley between her boobs, and over her rounded but flat stomach, his member finally stroked Emily’s wet lips, lathering itself in the divine nectar of its to-be recipient.

Samuel’s breathing grew laboured while his eyes became bloodshot in excitement. He had yet to even take the plunge into the folds of her innards, but the level of sensitivity experienced by his cock, which was unlike anything he’d ever felt in his entire past life in the comfort of his own hands, brought him right up to the edge- causing him to erupt.

“Agggh~ F-fuhhck.”

Samuel’s eyes rolled to the back of his head as the unrivalled pleasure-inducing ejaculation clouded his dopamine-addled brain, causing his elbows to give out. The young adult fell straight into the crook of Emily’s neck as his cock released its backed-up contents.

Streams of semen soared through the air, as his cock which lay atop his neighbour’s sex organ, contracted in its blissful release. The cum reached as far as beneath Emily’s huge breasts and settled there, while Samuel was propped up against her bountiful breasts.

“Huff. Huff.”

Taking in large gulps of air as his empty brain began to function again, Samuel eye’s, which had finally returned to normal, constricted.

‘I came… before even… putting it in?’

“Fuck! Fuck!”

Samuel punched the mattress below the pair in frustration, as he realised all his planning had come to nought because he couldn’t control his pent-up desires before the deed could be completed.

For a minute he just lay there, breathing roughly into the gap between Emily’s head and the pillow, while his cheek was pressed up against hers and his arms sliding below her shoulders so that he could hug the woman under him. His now-flaccid cock with droplets of pitiful semen still dribbling out of the tip.

Entangled in such a comfortable hug with generous skin-to-skin contact sending feel-good hormones through his system, Samuel’s restless emotions began to settle until his anger was finally no more. In his scarce vision which was blocked by the brown hair of the woman below him, he noticed that not much time had passed since ejaculating. Which made sense, since nothing much had actually transpired. He still had a good 18 minutes to do with as he wished.

‘Well, I wonder… I have 18 minutes of Emily in a state of deep sleep and, at least from what I’ve observed, mostly unreactive to outside stimulation. But what about after that? Will she just wake up? Or stay asleep since it’s the night already?’

With random thoughts about the events that would occur after the potion’s usage time ran out, Samuel rose from on top of Emily’s enormous boobs. His eyes, which appeared grey in the dark ambience of the room, had what appeared to be tenderness swirling within them while he looked at the resting face of the woman beneath him. Despite having essentially raped her, and with the possibility of leaving his neighbour, who had a husband that was awakening to the idea of abuse, traumatised from such an experience, Samuel couldn’t help but ponder over how much this experience made him want to look after her.

It sounded stupid. A man who wanted to rape a woman now desired to look after her. What kind of idiot would get involved in the mess they created if they could get away with it? And yet, Samuel was such an idiot.

In his previous life, Samuel wasn’t just some idiotic otaku with no mind of his own. He was actually quite reflective and somewhat knew how to make his life better. But he never bothered to implement any of these changes, because there was no one to change for. No one would look forward to seeing how he turned his life around. No mother or sister to care about him, nor for him to care for.

He had lost his confidence in himself as his waist measurement grew larger, and had basically secluded himself from the outside world, and interacting with women in general. He certainly had lacking social skills, evidenced by the awkwardness in his conversation with his neighbour earlier, but even he himself felt as though his confidence had the potential to be renewed as his waistline had once more become multiple sizes smaller. And most importantly, his family was still alive.

‘I have something to live for in this life, don’t I?’

While stewing in his life-changing thoughts, Samuel had not realised that just now he had utilised the complete package that was the sage mode in all of its glory, as the purpose of his going back in time was formed in his mind. The events since finding himself back in his 18-year-old body had been quite hectic- what with gaining a system, conversing with his beautiful neighbour, and promptly completing the missions provided by the system.

But now that he had thought through a lot of the things in his mind, and formed some sort of resolve to cherish his current timeline, he looked back at Emily’s sleeping face. Samuel was captivated by the perfect features of the woman, wondering why he had not taken a closer look before. His eyes slowly roamed down from her blemish-free eyelids which were crowned with long eyelashes, to her upturned, celestial-like nose and flushed, full cheeks, before ultimately settling upon her plump, rosy-red lips.

“Wow. She’s just so fucking beautiful.”

The young adult could not keep the expletives out of his mouth as his eyes were locked onto her lips. His head began to slowly descend until his lips were a hair's breadth away from his neighbours. Just as they were about to connect, he found his nose bumping against her pert counterpart, so he slightly tilted his head, and went in for the kill.

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