What If - Scotty the Hottie Ch. 01

She had just sat down in her car, and it was just after dinner-time when Phoenix finished a long day of skiing on the mountain. She was hungry, but for something more than food. Despite getting in a good amount of exercise she was still wired, feeling all pent up probably because it had been over a year since she'd had sex, and more than a few days since she'd last pleased herself. Exercise has that well-known effect on libido, and as Phoenix sat in her car, her seat-warmer emanating pleasant waves of warmth up through her core, she resolved that tonight was the night she was going to get some action damn the consequences, regardless of the aching in her legs and gnawing in her stomach.

Not to worry about our irresponsible heroine, it actually turned out alright for her, despite making some questionable decisions along the way. She messaged a guy she'd been chatting to online. He was game, obviously, and offered to host, and Phoenix was so hot and bothered she said damn the consequences and accepted. Not all hook-ups turn out well when they start that way, but this one did and Phoenix didn't get hurt. In the dark evening sky she wiggled out of her ski clothes in the front seat of her car and into her favorite dress, which she had in the car just in case she'd have an occasion to want to look sexy, which now she did.

By the time she was changed and ready to drive, it was snowing heavily. The 45 minute drive through a blizzard to the guy's place in a nearby municipality was harrowing, but luckily she kept her composure, took it slow, and made it there safely. She parked outside, put on her make-up using the rear-view mirror, slapped a cute toque over her dishevelled hair and texted. The guy, a large athletically-built basketball player with an impressive collection of Air Jordan shoes, came out to meet her and took her inside.

Phoenix wasn't totally sure what she expected, but she was taken a bit aback when she was led into the back entrance of a basement suite and into a modest sized bedroom where there was a king-sized bed that took up most of it, surrounded by screens (and what looked like a surveillance camera mounted on the ceiling). Was it on throughout her encounter? She'll never know I guess, unless someday she sees herself awkwardly navigating her first hook-up in over a decade in the old archives of an amateur porn site. That day though, thankfully, has yet to come.

The hook-up went well. Not only was Scotti handsome and built, but he was also extremely respectful and decently patient. He made Phoenix feel comfortable, and she had lots of fun blowing his large 7" cock, licking his big mocha balls, watching porn on the impressive monitor setup, and letting him cum on her tits before she came all over herself. Then she cleaned herself off and got dressed and went to the bathroom. When she came out of the bathroom after getting dressed, she noticed the door was open and incorrectly assumed that was a polite way of asking her to leave, which she did.

Well Scotty made it to her car before she left, visibly upset that she'd made a quick exit. He told her she could stay the night if she wanted to and said he wanted to see her again. She declined as politely as she was able, saying she had to be up early the next morning, and they left it at that. Phoenix thought about that hook-up often over the next year, as she resisted the urge to have what might be just another one-night-stand. When she finally did decide to try again she got back in touch with Scotty before anyone else, but sadly it just didn't come together again.

She often wonders what might have happened if she had accepted Scotty's invitation to stay the night instead of driving home? Would she be in the same place, the same person she is today? Would she have checked an item off her sex bucket list but maybe that's all, or would it have had a more profound effect on her future? The Phoenix of this world will never know what might have been, but in another reality... a different Phoenix does.

What if Phoenix had stayed the night with Scotty the Hotty?

She hadn't left yet, and was just putting her dress back on, after wiping herself down with a hand-towel since she was covered in lube and cum from her face to her ass after their play session, when Scotty asked her -

"Why don't you stay the night? It'll be fun."

Phoenix thought for a moment instead of answering immediately. She imagined Scotty's hot cock in her mouth. It was a happy thought, but followed immediately by the less happy thought of such a monster cock tearing into her asshole and hurting her for life, like what happened with her first sexual experience with a man when she was just 19. She flinched at the thought, but instead of saying no immediately, she looked up at Scotty who was staring at her with adoring and sincere eyes, and instead she asked -

"Well, what do you want to do if I stay?"

She imagined he would take this moment to press her to fuck, or maybe have a threesome with his roommate or something. Although theoretically she liked the idea of both options, she knew in reality that this wasn't the time and she wasn't ready. Instead though, Scotty said -

"We could smoke some more weed, play some xbox, listen to some music and cuddle." He smiled at her sweetly.

That sounded really good to Phoenix. It was exactly the type of casual and friendly intimacy that was missing from her life along with sex. She stopped changing after pulling her dress halfway up, and looked at him. He was still smiling that sweet smile.

"I'm not sure I'd be up for much more playing around before falling asleep," she said with a stifled yawn, "I usually go to bed early and get up early."

"No worries," he responded, "you can sleep in my bed whenever. If you want I'll cuddle you."

Phoenix did like the sound of that, but she was still hesitant.

"I don't think I can suck your cock anymore tonight," she said bluntly, "that was definitely the longest I've ever gone down for and my neck is sore," she tried to sound bubbly and convincing, but it came out tired.

"That's cool, I've already cum so I'm good for whenever. I just want to hang and get to know you better. I'll give you another neck rub," he paused a moment, "for as long you want."

Phoenix's resistance washed away. He sounded so earnest, so different from what Phoenix expected from a casual hook-up and from what she'd come to believe was the norm from her past experience with men. It definitely took her by surprise, and even though it seemed impossible given her current state of exhaustion, she felt herself getting flushed and turned-on again by the way he was treating her.

"Ok," she agreed to stick around, "it's probably for the best. I'm pretty tired, might not be a great idea for me to get behind the wheel right now anyway."

Scotty's bright smile brightened further, and he leaped into bed with an acrobatic ability unexpected from such a large man. Phoenix looked at him, lounging regally on the soft comforter, then pulled off her dress (but kept her boy shorts on), and yelled "Cuddle time!" before rolling in beside him with her usual agility. Her mood was sky high, the best it had been in the many years leading up to and through the breakup of her decade-long marriage.

She rolled inside Scotty's embrace and assumed the little spoon position, wiggling her butt back into Scotty's lap and feeling his impressive size, despite the fact he wasn't even hard anymore after cumming. The thought made her drip; god he had a sexy cock.

She melted into his hands as they worked her neck and shoulders, loosening her knots of tension and stress. She moaned as he massaged her, moving his hands up and down her spine and squeezing her ass and thighs. The massage was a sweet release for Phoenix, touch starved after years in a neglectful marriage with little but the occasional boring missionary sweat session for physical affection. Phoenix felt so good she closed her eyes and lost herself to the moment, thinking about nothing but the wonderful sensation of Scotty's hands on her body, the heat of his body and fresh scent, and the rise and fall of his breath soothing her with every breath of her own. It was only minutes until she was fast asleep.

She woke up with a start, dreaming of her own apartment only to open her eyes in this completely different place. There was a warm blanket wrapped around her but she shivered anyway. Blinking the sleep from her eyes she saw Scotty sitting up, his back propped by a pillow against the headboard, holding an Xbox controller in his hand and staring at a screen across the room. He noticed Phoenix, paused the game and looked at her with a smile.

"Uhhh, I feel groggy, how long have I been asleep?" Phoenix asked, disarmed by the smile and coming to terms with her situation as she remembered the events that led her there.

"Not too long," he answered, "about 45 minutes. I've just been playing games" he gestured at the screen, "it's only 10:30pm". He eyed her up and down, and Phoenix suddenly felt conscious of her bare chest that peeked out of the blanket, but she didn't move to cover it up. She had stopped shivering, and was warming up quickly now that she was awake.

"Fuck you look good," Scotty shook his head slightly, as in disbelief. "I didn't believe you'd look like your pictures, but you look even better in person..."

Phoenix blushed deeply; the compliment sank deep and caused her whole body to quiver slightly. She very much liked to be complimented, especially in person.

"Thanks," she said, pulling the blanket down lower to expose her full upper body, "you're no slouch yourself."

He smiled in thanks. "Come on out of that blanket, you must be warm now. Come cuddle up and we'll play some games." He held out his arm as if it were around her shoulders. Phoenix slipped out from under the blankets and sidled up beside him."

"You play Call of Duty?" He asked. Phoenix didn't. She thought briefly about lying, but realized he'd find out pretty soon if they actually tried.

"No..." she replied honestly, "I'm more of a Mario fan."

Scotty chuckled at that. "Sorry, I don't have any Mario."

"That's ok," said Phoenix, a little disappointed but hiding it well She looked around the room, and again at Scotty noticing that he had boxers on now, but there was an obvious bulge in the front of them. Was it just her, or was it growing?

It was definitely growing! Scotty saw what had caught Phoenix's gaze, grabbed his package and winked at her.

Phoenix's was getting hotter by the moment. "Fuck video games. I want to play with that," she said pointing between Scotty's legs. "Like, right now."

Scotty pulled his dick out of the fly of his shorts and pointed it at her, waving it around enticingly. Phoenix bent over, guided by Scotty's hand on the back of her head, and put his cock in her mouth. She kissed the tip of it, then all around the head and started licking up and down the shaft as she maneuvered her body between his legs. Her head bobbed up and down repeatedly, and she flicked her tongue against that one little spot, just beneath the base of the head, that she knew from experience drives every many wild. Scotty had two hands on the back of her head now, and his grip was getting stronger and he was starting to thrust his hips slightly each time Phoenix's head dipped, pushing his cock further and further back into her throat. Phoenix looked up at him from under her long eyelashes as she sucked and took it all in, trying her best to suppress her gag reflex but failure several times.

"Let me fuck your face," said Scotty, looking back down at her. Phoenix couldn't really talk with his massive rod still in her mouth but she managed to mutter out a positive "Mm hmm" to acknowledge her willingness to allow this man to use her how he wanted. She had never been face-fucked before, but at that moment she wanted it more than anything else.

Scotty held her headly firmly as he began to thrust with his hips and deliver his thick cock into her mouth repeatedly, with force and surprising speed for a man so big. Phoenix expected to gag but the tip of that cock hit the back of her throat so rapidly that it was like her gag reflex didn't even have time to respond. After a few thrusts Phoenix completely got over any inhibitions or difficulties accepting a greater and greater amount of Scotty's 7" length. Her cheeks pushed out as the man's shaft slid down her lips. It was thicker than her mouth could handle without her jaws open wide and cheeks being stretched out. Her eyes rolled back into her head as Scotty's cock pounded its way through her lips and into her throat. Phoenix was able to breathe through her nose, but when Scotty pulled her by the hair and lifted her head off his cock she gulped for breath, like someone just coming out of the water after a very deep dive. Her neck twitched for a second as she breathed the sweet relief, almost like she was having an orgasm in her throat.

"You liked that, didn't you?" his fingers tugged on her hair as she motioned up and down with her hair, unable to speak but yes, liking it very much. "You want some more? Don't worry I won't cum," Scotty continued and Phoenix, without hesitation, nodded her consent.

Scotty's strong grip pushed Phoenix's lips back over his dick as they went for round two, stronger and faster and certainly no less intense or enjoyable for Phoenix as the last. Somewhere, in the back of her mind, she wondered if Scotty had just made her his bitch, and what that might mean for her, but at the moment she was pretty sure she was right where she wanted to be. bitch or not. When Scotty pulled her up for air after the third time face-fucking her, Phoenix was starting to actually regain her composure and was able to respond when he spoke down to her:

"That's good baby doll, I think we've both had enough." Phoenix felt a pang of disappointment, but she had to agree. Her throat was starting to feel sore from the pounding.

Scotty looked at her sympathetically, and let her lay her head down on his belly. His tone changed, and instead of domineering suddenly had a hint of trepidation.

"I told you earlier that I might put you in my mouth, if I had a drink or two..." he said, carefully.

Phoenix recalled, he had indeed said that.

"Do you want to sixty-nine?" He continued, "You can be on top or bottom."

Phoenix thought for a moment. She never fantasized about a man sucking her cock, definitely not masculine men, but she was really worked up and also feeling pretty well-used already and it might be nice to relax a bit. Getting your throat fucked is fun, but it's not easy, especially not for a weary transvestite up well after her normal bedtime on a Tuesday night. She looked at Scotty's big full lips, he was biting one just a little bit as he waited for her answer.

"Sure, yeah let's try that," she said, somewhat hesitantly, "let me be on the bottom please."

"No prob," came Scotty's instant response. Phoenix rolled off of him and onto her back as Scotty sat up, turned, and swung a leg over her.

"You can relax," he said, "don't worry about working too hard down there I'm going to be pretty distracted." He laughed and lowered his head down to her crotch and put the tip of her head into his mouth. "Mmmmm," he hummed, "this tastes good..."

As Scotty sucked her, Phoenix used her hand to maneuver his cock into her mouth. Their position with him on all fours, his ass and cock suspended over her head, made it so that just the tip reached her when her head was laid back on the pillow. She enjoyed the opportunity to focus on that part very much, licking the end of it and circling her tongue around and down to the bulge where the tip meets the shaft. Scotty's mouth slowly took in more and more of her as he let her cock slip deeper past his lush lips and into the back of his throat.

The pressure mounted for Phoenix as he sucked. She began to raise and lower her hips in time with the bobbing of his head, and was starting to wonder how long she would last without cumming. Her body was starting to shake and her body quivering when Scotty pulled his head away from her, lifting the tip of his cock out of her mouth at the same time. He swung his leg back over and off her body and sat down next to her, running his hands up and down her side.

"I want to try something, if you're into it," he said, with a hesitancy Phoenix hadn't heard in his voice up until this point. She shook herself out of the feeling of being edged nearly to explosion, and sat up to look at him with interest. He looked almost bashful.

"What do you want to try?" She asked, with genuine curiosity. Scotty stammered a bit as he answered -

"Uh, well, you see, I want you to fuck me... in the ass" he admitted, "but only if you want to!" The last part sounded almost like a plea, as if for a way out of a request he wasn't sure he wanted but felt compelled to ask anyway.

Phoenix had never fucked a man before, not like that. She desperately wanted to get fucked in her ass, but Scotty's size was a significant barrier given her narrow hips and they still hadn't gone that far. This was a definite turn of events though. Phoenix carefully considered his request, and decided she needed a bit more info if she was to agree.

"Have you ever been fucked in the ass before?" She asked, again with genuine curiosity.

"Once," said Scotti, "but it was ages ago. It hurt but I liked it. I like to use toys a lot though."

Phoenix could sympathize. Getting topped could definitely hurt, a lot, if it was slow and gentle at first. She too had her own collection of toys at home that she loved to use on herself, so. he wasn't surprised that Scotty enjoyed it. It's certainly one of the most pleasurable things a man can do, if he takes his time to do it right. She nodded her head slightly as she responded.

"Ok," she said, "are you clean?"

"Yeah," he said, "I douched while you were asleep." He motioned towards the bathroom.

Phoenix looked down at her cock. It was still rock hard after getting fucked in the face. She considered its size and length. At 6" long and 1.5" across it wasn't huge, certainly not as big as Scotty's, but it wasn't exactly tiny either. She thought about fitting something that big in her ass, it would definitely hurt without a proper warm-up. She looked up at Scotty, who was looking back at her somewhat imploringly.

"Are you sure?" she asked, "I don't want to hurt you." It was true, she didn't. She was no sadist, and much preferred giving people pleasure to pain. Although to be honest, she'd never been asked to hurt someone during sex before.

"That's ok, I use toys a lot. And I'm like three times your size." He laughed.

Phoenix nodded to herself and Scotty flipped around and positioned himself on all fours.

"Like this please," he said, then after a moment's thought asked - "Do you want to rim me first? Not sure if you're into that..."

The question took Phoenix by surprise and she looked at the ass in front of her. It was smooth and clean. She put a hand on each cheek and spread it apart. It was a good looking asshole, and it puckered enticingly. To Phoenix's surprise, she did feel the urge to lick it.

"Here's a dam," said Scotty as he handed Phoenix a thin piece of latex, like a condom cut into a square. "I'm clean but use this."

Phoenix laid it down and put her tongue on top and began to feel around the edge of Scotty's hole with it, making circles around and around again pushing further and further against the rim, opening it up slightly with the pressure of her tongue. Scotty moaned, his hands gripping the sheets and he lifted his ass up and pushed it back towards Phoenix's face so her mouth and nose were buried in it. She liked rimming him very much, his eager moans an audible reminder of his appreciation for the benevolent act. After a few minutes she was feeling a strong urge to stick her dick in him.