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The Beauty and the Nerd. desperado1089 x Alisa_Perne


"Last rat standing."
Dec 30, 2020
Baltimore, MD, USA
Sean Stewart had a good life. And up until a few weeks ago, it was a happy one. But that all changed when that drunk driver ended the lives of both his parents. The cops caught him, and it wasn't the bastard's first rodeo, and this sort of thing had happened once before, but the people from before had survived, somehow, but not this time. He knew that this could happen, yet he drove drunk anyway. So the DA was able to hit him with negligent homicide. Sean's family could afford to send someone with a statement or a deposition or whatever the hell. He didn't wanna face the fucker. Nobody blamed him for that.

A tearful funeral and a while later, it just struck him all of a sudden just how much his inheritance was. Who the hell inherits a hundred million dollars, anyway? Certainly not the kind he liked to associate with. All his life, Sean was a kind soul, always helping out where he could, and using his money and influence where he couldn't. At any rate, he was actually very shy and reserved when it came to women and the like, so much so that he was still a virgin when his parents died. He was also sort of a nerd, but a few women had told him he was cute over the years, so maybe that wasn't such a bad thing.

At any rate, he wanted to get out of the house for a while so he booked a room at the nearby Sheraton hotel and decided to spend some time playing video games, surfing the Internet, and reading by the pool in quiet solitude. It was this last activity he was engaged in on the day that began normally, but would certainly not end up that way. But he didn't know that yet.
Ally had recently moved into town, and was waiting to move into her apartment, she had recently taken a job offer at a local gym to be a personal trainer, she quit her old job working in a call center and moved here, this was her dream job, she both looked and acted the part. Ally was five feet eleven inches, and she was thick in the hips, and she had well defined muscles and shoulder length red hair, green eyes, and a perfect smile. She walked into the pool room and did a few stretches, she did the splits, reached over and touched her toes, did a few backbend flips, flexing and tightening each muscle like a professional body builder, before she dove into the pool with little more than a small splash, she swam half the length under water before surfacing for a breath. Her movements were controlled and precise, she was an athlete after all. She did a full ten laps, end to end of the pool before she stopped halfway, and pulled herself out, at the ladder right in front of Sean, her bikini bottom sagged for a second or two from the weight of the water, showing the top of her nice hairy red bush, it was bright red and the water dripping off it played with the light, making it look like there was fire, given the fabled name all red heads had, fire crotch. Sean was right by the towel cart, so their meeting was inevitable. "Hey." she said drying herself off, "Whatcha, reading?"
Sean noticed this entire thing and couldn't believe what was happening. He wanted to flee, but what kind of message would that send? So he just tried to concentrate on his book, but found it increasingly difficult not to watch, especially when she finally stopped swimming and climbed out of the pool, exposing a bit of her pubes. He stammered as he nearly dropped his small, leather-bound softback copy of A Game of Thrones by George R.R. Martin. "F-first Game of Thrones b-book."
"Ahh, gratuitous, violence, sex, and incest. Yummy." she continued drying herself off, "So, what brings ya here?" she said sitting on the chair next to him to engage in conversation. Truth was she had been alone for the past few months, working, sleeping, eating, so any human contact was welcome and she was a social butterfly, whether this man liked it or not, they were going to have a conversation.
"Y-yeah, yummy." Sean wasn't talking about the book as he kept staring at the still-exposed hair between her legs, then cleared his throat and looked up at her face. "It's a tragic story, the answer to that last question. You sure you wanna hear it?" He couldn't help but notice that they were in an interior setting, with a heated pool, and she was a hairy redhead. Sort of like Jon Snow and Ygritte. If he mentioned this aloud to her sometime later, he knew she would get the reference, as she clearly knew what lay between the pages of the novel in his hands.
"I wouldn't have asked if I didn't" She smiled, "Ya know what, I will go first." She stuck her hand out "Ally, I am waiting to move into my apartment here, I used to work in a call center, but its always been my dream to be a personal trainer." she flexed her abs as if to emphasize the point, "So I applied for the job, and now I am here, they put me up in a hotel while my apartment gets ready, should be next week." she winked, "Your turn."
Sean took her hand, and in a strange flash of inspiration, lightly kissed it as if he was a knight of Westeros or something. "Sean. I am here to get away from my home for a while. Too many memories, my parents both died a few weeks ago." He pulled out his phone and pulled up the news article he had bookmarked: "Local Millionaire Power Couple Killed by Drunk Driver". He handed her the phone, and added lamely, "That's why I'm here."
Ally read through the article, her expression grew somber, and she was truly sad to hear someone was the victim of such a tragedy. She put the phone down and just instinctively hugged him. "Sean, I am so sorry this happened to you. I know you don't know me well enough but I would love to listen any time you want to talk about this." its true, Ally had a habit of just opening up to strangers, despite the fact her figure was quite intimidating, she was a teddy bear with empathy for any human as deep and wide as the ocean. "Sean?" she asked, "Do you want to grab some lunch? My treat?"
Sean was taken aback at her hug, but he put his book down and returned it gratefully, smooching her wet head. "Thanks, Ally. And the fact I don't know you? That can change. I think I want it to change." When she suggested that she treat him to lunch, he laughed despite himself. "Ally, what is the second word of the headline, there? I would like to pay for lunch, if that's okay with you. Is room service okay?" He suddenly realized the implication of what he had offered, and froze, unable to add something to soften his forwardness, nor retract his statement completely. He gulped, hoping she wouldn't toss him into the pool or something for thinking of sex at this early juncture.
"I was thinking about heading to an actual restaurant and sitting down, but ya know what, fuck it. What's your room number, let me shower and change, give me lets say." she put a finger to her lips in thought, "Thirty minutes? Then we can pick out our food together and just spill tea about anything and everything." she smiled offering her hand out for a handshake, "Sound good Sean?"
"Not too bold." she said, looking to the chair where she had her clothes lain, tank top and short shorts, "As long as you don't mind me using said shower, and not really having clothes appropriate for our little date." she said with a disarming smile, she wasn't stupid, she knew what he was implying, and the more she thought about it, it had been weeks since she herself had been laid, and she was about to give this cute little nerd the ride of his life.
"I wouldn't have offered if I minded you using it. And who says you were gonna need clothes," he paused dramatically, caught up in the moment, as his voice dropped low and husky, "at all?" At that moment, he didn't care if he was a virgin. He didn't care that he may never see this woman again--although he had a strong suspicion he would. There was something magnetic about this Ally, and he fully intended to offer no resistance as she drew him in, like a planet to a meteorite.
She got incredibly close to him, practically straddling him in his chair, her much larger and imposing figure over him, she leaned over and whispered into his ear, "Who said I would care?" and with that she stood up and winked, "You ready?" she asked, knowing full well that in this case dessert was going to come well before dinner.
Sean just nodded, too tongue-tied to speak, as he grabbed the small sling-bag he used to carry his book, some breath mints, and some aspirin and got up, grabbing her clothes and stuffing them into the bag as well. He grinned when she turned to question why he did that, suddenly finding his voice: "Less to take off, yeah?"
"Nauuuuughty." she said and wiggled her finger, but continued to follow him anyway, she followed him right to his room and waited for him to open the door.
Ally stepped in to the hotel room and flopped on the bed, and stretched and yawned, "Jeeeeeze." she said as she stretched, "Oh man, that was a good one." she sat up, yawned again, and stretched again, flexing a little, showing off a little. "You gunna come here or what?" she asked, "I don't bite, I squeeze with these." she flexed her biceps and smiled.
Sean shut the door and flipped the privacy deadbolt, then suddenly lost his nerve. He started fidgeting, and said in a small voice, "I-I haven't ever done anything like this b-before." He dropped his bag and flopped into an easy chair near the bed, covering his face with his hands. "God, did I just bite off more than I could chew here?", he said aloud, half to Ally, half to nobody in particular.
She sat up and stood up walking over to him, she got on one knee, next to him and wrapped one arm around him, rubbing his back. "Aww Sean, its okay, I promise I wont hurt you." she continued rubbing his back and ran another finger down his thigh, "Get your courage up Romeo, you came this far." she smiled.
Noticing how she was down on one knee, his lips twisted upward in a small, wan smirk. "Where you hiding the ring?" He took a deep breath, getting his courage up as she said, and cupped her face in both hands and kissed her. That, at least, he knew how to do.
She smiled into the kiss, "I believe that is your job." she said as she pulled back from the kiss. She sensed he may need some help, so she grabbed him under both arms and pulled him up, then picked him up and sat him on the bed, she then sat on his lap, a knee next to both of his thighs, she slowly pushed him to the bed and kissed him as she did so. "Better?" she asked.
"Yep, although you don't expect me to keep my clothes on, do you?" He suddenly wondered how good it could feel if both their bodies were wet as they fucked. Had sex. Made love? His mind decided they all made sense as long as that last one was included.
"That seems like a fair assessment, lets make it interesting. I still need my shower, so lets do this. You can wait for me to get out of the shower, and then we can start off nice and slow. Or! You can give me a few moments to get into the shower and we can just go to town." she smiled, "Your choice." she stood up and started walking to the bathroom, she took off her bikini top and tossed it over her shoulder ensuring it would land in his lap. When she got in the bathroom, she removed her bikini bottoms and turned the water on nice and steamy, watching the mirror fog up for a few moments, before getting in and letting the revitalizing hot water wash over her tired muscles.
Sean didn't need even a second to decide. He stripped down to his underwear in seconds before grabbing a condom from his bedside table and tucking it behind his ear. He padded over to the open bathroom door and dropped his boxers, revealing a generous, fully erect seven-inch cock, before proclaiming, "I choose option two!" and walking inside the bathroom, shutting the door behind him.
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