A New Life, A new Girl Ch. 01

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A guy with bad dating and hookup experience meets a new girl.
6.6k words
4.68
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38

Part 1 of the 4 part series

Updated 06/15/2023
Created 04/04/2023
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Tyler was an average guy. Well, slightly above average guy. He stood at six foot three, was two hundred pounds and was in his late twenties in a successful office job. He had a head full of black hair and a well trimmed beard. He wasn't the most athletic in build, but he had more muscle than fat which left him in a trim look rather than that of an athlete or bodybuilder. Not only that, but he had a rather nice face. Yup, Tyler really had it a good life. One easily in the upper half of people. His only problem was his dating life. He kept meeting shallow women, and those who weren't shallow often weren't very attractive.

He was searching for that middle ground with a girl that was sitting at a five to eight in looks and a similar level in personality, but for some reason his luck in this area was terrible. It could be his own personality, as while he was just above average in life, he often acted with the confidence and self centered interest of a man with twice what he had. This didn't mean he outright ignored the feelings of others and their interest and needs, but he just didn't outright think of them unless it was something important like a birthday or in case they expressly told him to do something. It just wasn't in his nature to look much further.

So, most of his relationships either ended in him ending a relationship do to people not having a good match in personality, or in the girls leaving him because he all too often got lost in his own world and when he wasn't, it wasn't exactly all about them, so they either cheated or just straight up left him. This spiral of bad experiences and overall emotional rollercoasters had left Tyler more unenthused and hurt by relationships by the day. He even began to blame women for many of his problems and started exploring more physical relationships.

For him, this was great as no emotional baggage came with just fucking around with other people. He could just ask around and eventually land one or two dates in a month, maybe more. They both get their rocks off and then head home. But he was getting older and while he wasn't losing his looks, it was harder to compete with younger guys by the day, and many women his own age had either stopped using the same sites and moved on with life in one form or another. This left him looking for rare women, or ones younger or much older than him. So he was back to square one.

That was when he decided to check his old dating profiles. They were out of date by several years, but it wasn't like much changed about these things over the years. They were all basically the same garbage designed with fake algorithms to match people based on looks and interest that they state.

But he did miss out on a specific update. One that updated to included updates on defining women. This app had accidentally labeled him as interested in all women as he'd swiped on a few trans and crossdressing people before only to find out they were not cis and not what he was looking for. But the algorithm didn't know that with its update, so his profile was open to any number of people that identified femininely. Although his account was cold, upon activation again, it updated and once more sent his updated pictures out to the masses. And it only took a few minutes until he saw a notification. It was from a young woman that looked rather gorgeous actually. Long black hair, clean fair skin. Light makeup and rather sizable chest. She wasn't very large in the rear but her long legs made up for it. Tyler would easily label her an 8 or 9 out of 10 in the looks department.

So he started looking over her profile to check out her personality and there were a lot of overlaps. Enjoyment of sci fi and fantasy novels and shows. An appreciation of video games and regular workouts. A love for cooking and interest in art and music that matched his own for the most part, though she seemed to have a unique interest in some Eurobeat versions of metal music which he found strange but not off putting.

All his boxes were being checked and her opening liner of "Hey, I've got all the extended lord of the rings downloaded from HBO and I think we've both just come off a few years of boredom with this bullshit dating scene. You wanna hang and watch them with me while we gorge on pizzas and snacks while getting to know each other or should I look elsewhere?"

The line wasn't exactly unique, but it hit right at his core of troubles and it meant she had taken the time to look through his profile and notice how much was out of date besides his pics. So, feeling up to a break from his relationship woes and hoping something more casual with such an interesting person was the break he needed. He checked her name and it said Amy Nithouser.

So, he messaged her back with an affirmative and the two were setting up their weekend date. The rest of the week passed in a familiar blur and the weekend was soon around the corner. The night before though, Tyler had decided to look through his date's profile again just to see if there was anything he should remember or in case there was anything that might catch his interest. That was when he noticed that her bio was labeled as TWoman. He tried to check what this meant as he was a little afraid it meant what he thought it did. And after about twenty minutes of checking around, he found out it was a new term for transitioning people. His eyes must have glazed over the T when looking and just ignored it. The rest of Amy's profile seemed completely normal, so he didn't second guess anything. He expected the app to have gender labels in full words, not self input. And he wondered how he matched with her to begin with.

He hit the bed with a mixture of annoyance and tired resignation. Another bust. He couldn't date a trans person. He didn't have anything against them, but he wanted kids some day. Biological kids that would share his and his partner's blood. He knew there were new medical procedures making that closer to reality all the time for couples who couldn't do it naturally, but it often still required a male and female.

He looked at his phone and wondered if he should turn her down now, or show up tomorrow and apologize. He debated for a solid hour before sighing and deciding to wait till the next day. He had been so excited for this weekend that he could imagine how she felt about it, and to turn her down because of his own baggage last minute was rude. Especially over text. He decided to show up, explain himself and whether they watched the movie anyway or parted was up to chance. He didn't mind making a new friend in the meantime since he had nothing better to do.

The next day, Tyler showed up to Amy's place. It was a sizable apartment in a nice neighborhood with its own gated garage and restaurants right across the street. He wondered how she could afford it as she seemed to be in a similar situation to him with a desk job and average income on her profile. Maybe it was out of date like a lot of his info. He shrugged and headed up to her door. After the third knock he heard the latch turn and the door opened to reveal the same Amy he'd seen on the app. Long black hair. Womanly figure, and rather ample breast hugged in a tight t-shirt that was barely hidden behind her open hoody. The leggings and hair were the only really dressed up parts of her as the rest looked like she was going for casual Friday. Tyler himself was in a three button collared t shirt that hugged his arms around the bicep and left enough room for his slight belly to look more like a nice V above his jeans. He looked down at her five foot eight frame and smiled before saying "Hey."

Amy for her part did a bit of a double take on him and smirked before saying "Mmmm, you're more dolled up than I expected. Momma likey~ Come on in. I got snacks and everything ready." She opened the door wider for him and before he could think, he was already stepping over the threshold on instinct. He had an entire speech ready and was prepared for serious bashfulness or awkward ice breaks, not a sudden interest for his looks and outright casual flirting.

So after he'd stepped in and heard the door shut behind him he tried to speak up with a "Uhm.." But before he could get a word in Amy was already on a trek to show him around her place. "So, welcome to my place. It's got all the fixings. Fully decked out kitchen with packed fridge and pantry. Living room right over there passed the kitchen table. It's where we'll be watching things. Eighty inch 8k television with surround sound system and all the noise blocking foam and walls a girl could ask for to truly enjoy a cinematic experience. Over there is my room. No peaking mister naughty. And over there is my office. Bathroom for guest is just next to the office. I've already got Fellowship loaded and ready and am prepared to break out blankets, bongs and or blades for any situation. Ground rules are we sit in separate chairs or opposite ends of the couch at the beginning until movie two at which point we can decide how we feel. Please don't go into my room without my permission at any time. And make sure to ask about the last slice of pizza every time or face immediate retribution. Any questions?"

She looked up at him expectantly and Tyler was a bit thrown for a loop at how prepared and casually she was handling this. It was more like a well thought choreographed event than a date. But he looked down at her smiling confident face and said "Not on those...but I do want to make sure. You are trans right?" He seemed worried he might hurt her with this question but once more she threw him for a loop.

"Yes, I'm trans. Looking forward to finding out which side huh?" She asked with a jaunty smirk and wiggle of her eyebrows. "Well, that's for you to seduce your way into. I don't usually put out on the first date since I like to get to know people a bit better. But you're hot enough and I'm trying to experiment a bit more and just try new things. So, it's up to your skills big guy~ Maybe I'll let you in my room after movie three and you're really good~" She winked up at him and giggled at how he flushed from her teasing.

But he shook his head and had to put things right now, before it got out of hand. "You don't understand. I didn't realize you were trans until last night. I'm sorry, but I don't date trans women. I want my own bio kids some day and I don't want to lead you on that this could get serious. That's not right to me. I've been going casual for a while now, but got back on the dating scene just recently. And you seem like you're looking for a serious shot. So, I'm sorry. I wouldn't mind being friends though if you're ok with that." He definitely sounded a little too serious at parts and overly hypocritical given he was willing to sleep around but not just date a woman for a short while. But he wanted to try and get serious, not lead people on for no reason other than to just date. Even his causal flings all knew they were just flings. He looked down at Amy wondering what her reaction would be.

Amy for her part got serious for the first time. She put on her first frown and then sighed. "Should've known it was too good to be true. You seemed so willing in your messages I just assumed you knew and were into it or at least experimenting like me. I can't blame you for having those kind of hangups." She scratched her head unsure of where to go from here.

She paced back and forth for several moments, tapping her forehead in a rather cute way if Tyler was honest. It was kind of interesting to see her range of emotion and thought. That was when she stopped and looked up at him seriously once more. "So, you don't like trans women at all, or you just don't want to lead me on?" Her question ringing some alarm bells in his head, but he decided to be up front keep their conversation honest. "I just don't want to lead you on. I think you're gorgeous and very funny. But I don't think we can have a serious long term relationship. And I don't really like the idea of just being in a relationship to be in one."

Amy returned to her pacing as Tyler watched on. Another stop. "Alright, how about this. We can start off as acquaintances for now, and build up to friends over the night. I planned this whole thing to be a slow build over each movie anyway, I just thought it'd be a romantic one instead of platonic. So, if you still want to stick around and try being friends, I'm up to doing that." She still looked a little unsure, but her face and tone were serious enough to say she wasn't just doing it to get rid of the large amount of food he could see.

"Sure. I'd love to stick around. I still enjoyed talking with you and you seem like a lot of fun. I just wanted to be upfront with you about things. So, I'm Tyler, nice to meet you." He said as he extended his hand for a handshake which Amy soon returned before beckoning the two of them to the couch and settling in to start the movie.

"By the way, I was surprised you let me in so easily, I expected to give my speech at the door, but you ushering me in kinda threw my plans out the door."

"Oh, that. It's fine. I had a taser in my leggings in case you were a creep or tried to force your way in. But you're hot, and showed up all nice and gentlemanly. So, while I've still got it and numerous other items with which I may incapacitate any such wayward assaulters, I felt I was safe enough around you that you could come in." She winked his way as the logos passed by and the music faded in.

The two just chuckled a bit before truly settling in to watch the several hours of movie. A few snacks, some idle trivia knowledge spewn about how the opening shots were thought of and how cool it would be to visit the town in New Zealand.

Time passed and the movie was filled with idle chatter and soft ball questions back and forth during the more boring bits of establishing shots and much of the council and exposition bits. But the movie finally ended with the typical crescendo of the fellowship broken and forlorn music playing. An audience of applause followed from both viewers and a chuckle soon followed from the both of them at their antics. Amy quickly turned down the music and said "Alright, time for a meal and pee break. Like I said, bathrooms over there. I'm gonna put the pizza in and retreat to my personal throne. Remember the rules while I'm gone ok?" And with that she spiked the over and threw the pizza inside before taking off for her room.

Tyler for his part didn't have to go so soon and was prepared to sit through another marathon before going himself. He took out his phone and started looking up anything he missed and wondering where this thing was going to end. He'd enjoyed himself so far and it was pleasant talking with Amy. She had plenty of funny jokes to give and seemed interested in what he liked or didn't like about the film, as well as some of his other interest and job. He worried a bit that she was still on date mode, but played along all the same. It wasn't like the questions weren't questions you'd ask a friend or acquaintance. It was just more fast tracked like you'd do on a date, which he guessed this still technically was, just a friend date.

Amy came back out after about ten minutes looking a bit fresher. Her hair was looser than before and she had put some chapstick on her lips that drew the eye to the gloss compared to before. She'd also ditched the leggings for a pair of fluffier pajama bottoms and zipped up the hoody. It seemed she was going even more casual, but still looking presentable now and it wasn't exactly bad looking, though Tyler had to admit that being barred from those rather sizable titties view was a bit of a crime. He knew they weren't exactly real, but they definitely brightened his view whenever he looked over at her to chat.

She sat back down on the couch and curled up atop it as she asked "So, how you feeling so far? Think we're friend material?" Her eyes expectant and a little judgmental. He couldn't blame her if her tone was a bit harsh given he'd probably hurt her earlier. So he just smiled and said "Oh yea. I think we can get along. You're definitely as funny as I thought you were. I hope you feel the same."

"Hmmmm........yea. We can be friends. I didn't like that you weren't exactly a Gimly fan, but I can let that slide for the joke you came up with about the Proudfeet. Alright. I officially dub thee friend. You may rise and join me on ze comfy couch. May you forever remember this day and protect this fellowship young man."

And with that long speech of knighthood into friendship, Tyler laughed and joined her on the couch to get a more direct view of the screen. There was still a cushion between them so it wasn't as though they were close, but it was comfortable thinking he'd made a fun friend today and got to watch the full extended cut of fellowship in as close to a theater setting as he figured he could get.

They continued chatting back and forth with one another until the ding of pizza sounded and sent Amy skipping to grab it. She had them each set up with a plate of slices and numerous more on a center plate atop the coffee table in front of them in the blink of an eye and was already starting the second movie. Once more the score roared in the apartment and the two settled in to watch.

Another several hours passed them by and they finished their meals, much of the prepared snacks and a number of interesting conversations that got both more into their lives as well as the movie. By the end, Tyler figured out how Amy afforded all of this. Apparently she moved on from office work to streaming regularly and made a tidy sum as a semi famous streamer for games, reactions and all sorts of things. She still did some contract and part time office work to keep her busy, and part over the bad stream weeks, but over all she was making practically twice what he did. It was a bit disheartening for him, but he was happy for her all the same. Plus, now he could say he knew a famous person, even if he couldn't say who since she wouldn't share with him her tag just yet.

She got up and cleaned their plates for them as well as the used wrappers and things out of the way as she asked "Still hungry? I've got more snacks, ice cream. I've also got soda's and cookies." Tyler just shook his head and said "Nah, I'm pretty stuffed, maybe after later. Thanks though." And with that, it was just the two of them, and that's when Tyler felt the need to hit the restroom. This left Amy alone with her thoughts and she used the time to grab a few more things.

When Tyler came back out from the rather average bathroom, he saw Amy curled up on the couch in a large blanket and one for him as well stretched out next to her. There was also a pair of mugs with what appeared to be hot chocolate as well as some water. "Figured something sweet doesn't hurt. Now come here." She said stretching her arm out from under the blanket and patting his seat which was now closer given she'd moved more center couch than before.

Tyler sat down and threw the blanket over his legs figuring it wasn't that cold, but it couldn't hurt as she seemed to keep the room cool. But Amy didn't start the movie right away this time. Now. She inched closer and settled her hand on his thigh as she said "Ok, serious question. Now that we've got to know each other a bit better, I think I have a solution to both of our problems. You want a serious relationship but keep striking out and ending up in short term nowhereville. I keep looking for good guys that can accept all of me and get me without wanting nothing but sex. So, my solution is this. We date, but in an open relationship. That way, we can cuddle, and be close and go on dates or just hang out, and maybe get a little steamy in the bedroom. But while we do all of this, we still date and look for other people and date them to see if they're more compatible. That way, we can still look for that one to come along, but in the meantime of striking out, we still have each other to fall back on and be open with. No more lonely nights or jumping from relationship to relationship. We can still get both emotional and sexual needs satisfied, but without worry of falling out too badly. What do you think?" And her rather expectant eyes looking up at him said quite a lot of what she had been thinking about throughout the movie.

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