It's Complicated Ch. 01

A bit more than a year ago I was struck by a drunk driver while cycling. I won't bore you with the numerous serious injuries I sustained, but will say that I've had five surgeries since then and I now have a hardware store's worth on metal plates and screws holding my left leg together. The physical therapy was very painful and I had always thought I handled discomfort well enough, but this was on another level.

With the ongoing pain of recovery and the number of surgeries, I spent more and more time alone, depressed and not seeming to know how to turn things around for myself. My name is Matt, I'm 23 and before the accident, you would never have believed that person and me were one and the same. Aside from the limp that was a source of constant embarrassment and the many scars, which I sometimes tried to convince myself were 'cool, and shows I've been through some shit.' my overall feeling was that my life had been sidetracked by someone that had been convicted of drunk driving twice before hitting me and ultimately was given a suspended sentence and a fine.

So much for justice right? I would have been fine with that driver going to jail for many years.

Before the accident, I had what I would consider a normal social life. I dated regularly and while I've never been one to gaze at myself in the mirror and admire my stunning looks, I'll say that at 5'10 and 170 pounds, I was in shape, and always active (I used to work in the construction trades) with dirty blonde hair, blue eyes and a quick smile. I suppose I didn't date as often as some others but I was happy. I've had sex with nearly twenty women, and I've never been rushed to orgasm. I suppose many people would say I'm a 'considerate lover' but the truth is, almost nothing else turns me on as much as making my partner cum. It triggers some kind of caveman thing in my brain. Maybe it's just some validation that I'm able to bring someone to that special place that lets their body almost lose control for a few moments, whatever it is, the women I've been with have always seemed very satisfied when we had sex.

But women had become a memory for me. The current version of me versus the unbroken version seemed like entirely different people and so when my younger sister called my parents and told them that she would be bringing her girlfriend home over the Christmas break, it didn't register more than a simple 'Great, someone else to watch me hobbling around.'

April is 19 and a freshman in college, going to school far away in California was exactly what April needed and while our family knew she was a lesbian and had 'came out' so to speak some years before, this would be the first time we'd be meeting one of her girlfriends. I was living back in the same bedroom I had grown up in, I hated having to give up my apartment and the independence that I had enjoyed, because in the earliest days after being discharged from the hospital, there was no denying that I needed help. It was just another thing that heavily impacted my confidence.

Watching my mother darting around the house as if royalty would be visiting within the hour was a bit comical, but when the front door opened and April walked in, pulling a quirky looking girl behind her, it just made me curious. April introduced the shaggy-haired brunette as Brittany, it was impossible to not notice this woman was extremely shy. She looked up as each family member was introduced, gave them a warm smile and a soft 'Hi' then looked away. It struck me what an unlikely pair the two made, April had always been outgoing, and always ready to try something new, Brittany looked like she would have been content to stay in her dorm.

Dinner that night was interesting, with Brittany being the center of attention. I know it's messed up, but her shy nature and her big, dark eyes kept distracting me. I suppose the fact that she was a lesbian also added to the mystique a bit, I'd heard plenty of morons say 'she's only a lesbian because I haven't fucked her!' nonsense, but I did imagine pushing my dick into her and once again, only focusing on making her cum. I really did wonder if I could change her like all of those dipshits would claim.

After dinner we all gathered in the living room. My parents were in their respective recliners, leaving April, Brittany and myself to sit on the sofa. Brittany was in the middle and with this closer proximity, I could smell her perfume, it was almost non-existent but I smelled flowers and maybe cinnamon. As we all made small talk I found myself looking at her more than anyone else in the room and could get away with it, because my talkative sister was opposite Brittany. Around 9:00pm, we all kind of went off into different directions, I wondered if Mom and Dad would be okay with April having her girlfriend spend the night in the same bed and I chuckled remembering when I was 19, I knew there was no possible chance my parents would let me bring a date to spend the night.

I was laying on my bed, binging on a show that I had a love/hate relationship with when I heard a knock at my door and after a quick 'Yeah?' the door opened and April walked in, she was alone.

"Matt, I'm not sure how to say this, so I'll just say it okay?" She asked, and it was clear from her expression she was conflicted.

I just nodded.

"You look like shit big brother, but somehow at the same time, you look better than ever."

"April, what the fuck?"

"I see this guy that's still hurt, and I knew the guy from before that hurt, now I see a guy that's struggling but you're getting better Matt, you walk so much better now than you used to. Please tell me you're gonna beat this."

"What choice do I have?"

"Dating?"

"Very funny April."

She walked over, sat on my bed and lowered her voice. "We've always been honest with each other, you were the first person in our family I told... You remember that right?" She was referring to saying that she decided she liked women.

"Yep, I'm sure we still have plenty of secrets we never told anyone."

"Please be honest now, okay?"

"Sure."

"Is Brittany pretty? You were looking at her after dinner."

"She is, in a kind of non-standard way, she's really shy."

"She is, I'm trying to help her with that. So... Wow, this is harder than I thought. I rehearsed this speech for the entire flight." She chuckled a tiny bit and then she rested a hand on my knee and inhaled before adding "If you hadn't gotten hurt, and if you weren't seeing someone, if you saw Brittany somewhere would you think about talking to her, or asking for her number."

"I don't ask out lesbians April..." I sighed.

"Yeah, but you couldn't possibly know she was a lesbian unless she was obviously with another woman. Assume she was in a bar, alone. Would you talk to her?"

"I don't go to bars to hookup with women."

"Say you were in a fucking coffee shop and she was sitting alone, better?"

"Why are you doing this?"

"I'll explain, but answer the question."

"Her shyness is kind of sexy. I like that her hair kind of gets in the way of her face a bit. That outfit she has on isn't doing her any favors, but I'm guessing she's decently in shape."

"So you'd ask her out, or get her digits or something?"

"Yeah, I guess."

"I'm not playing okay, so don't freak out. Would you have sex with her?"

"Guys ask women for their numbers, to arrange dates, men take women on dates to impress them as a potential mate, so yeah that would be the logical conclusion right?"

She inhaled, and squeezed my knee and then with the most dread-filled expression I've ever seen my sister with, said "We want you to have sex with her, she's never been with a man. She's curious about it, and I don't want her to always wonder what it would feel like, I'd rather she slept with you, because then I know her first time wouldn't be with some muscle-head asshole, and I think, I'm sorry Matt but I'm gonna be honest, I think if you have sex again it'll help you too. I think you're hiding from relationships."

I was speechless and at the same time, my dick was stiffening at the thought of watching my sisters girlfriend's face as my dick sank into her hot, wet pussy. The answer was an easy one, but there were all of those little complications, like having sex with your sisters girlfriend.

"She said you were 'sexy, but sad'"

"Well she's half-right anyway." I said with a smirk.

"Be serious Matt, this isn't easy to talk to you about. How messed up is it that I'm sitting here talking to my brother about him having sex with my girlfriend?"

"You're being serious, I guess I'm processing."

"You're doing what you do, not committing to something. There's one more thing."

"I'm not sure 'one more thing' would help here April."

"She's Trans."

I blinked several times and then I wondered how that was going to work. My exposure to anything 'Trans' was the constant bickering on the news about it, I'd seen a.gif that showed a very sexy woman's face and hair and the camera scrolled down to a pair of porn-star tits and it scrolled lower to a dick and then a 'You're GAY!' text popped up on the screen. So yeah, I didn't know shit about any Trans stuff.

So did Brittany plan to cut her hair off? Was that why she wore the loose outfit that she had on? Was she hiding a sexy ass and pair of tits? I didn't know much about lesbian relationships either, but I would have assumed if one of the involved people wanted to live as a man, that person would logically be the more outspoken of the pair.

"I don't want to sound, umm..." I searched for the right words. "If she wants to become a he, then why would he want to have sex with a guy? I mean, isn't that like crossing the streams?"

"You and your dumb movie lines, no silly, 'he' has become 'she'"

"Bullshit."

"I'm being serious."

"Your girlfriend has a dick?"

"Yeah Matt, she does."

"Swear on it?"

"I'll swear on whatever you want, it's true."

"Wow, I never would have imagined."

"So you'll do it?"

"No, I didn't say that. You're putting me on the spot. You spring all this shit on me and if I say 'yeah, but I'm not gay' then that makes me an asshole."

"It would be gay to take her virginity?"

"You know what I mean."

"No, I don't. You said yourself you would have never guessed she wasn't a woman. There's nothing about her that's male, aside from what's between her legs. Having sex with her would be nothing at all like having sex with a gay man. Now, if you had sex with a guy, I'd say that makes you bi, at least."

"I don't want to have sex with men, you're twisting my words."

"So you'll do it?" She asked hopefully.

"That's a lot to unpack April, let me think about it."

"It's sex without any commitment and I think it'll kickstart your social life."

"You're so thoughtful, looking out for me." I smirked.

"Everyone wins, think about it." She said, and shook my knee a bit before letting it go and heading back to her room.

I went back to watching my show but was so distracted that I shut it off and lay there processing everything. A bit after 11:00 pm I heard a woman's laugh, and wondered if Brittany was crawling between my sisters legs. That visual was a complex one. It's not like I imagined guys fucking my sister, in fact I went to lengths to NOT think about that. But Brittany was sexy, and now it had been explained that she has a dick, and I just couldn't help but imagine what that must have looked like, the two of them naked and grinding against each other.

I needed a distraction, and I needed to do something about the erection that was throbbing in my pants. So I got up, turned off my light and locked my door then went to one of the sex tube sites, and found a scene with two lesbians that were having sex, one of them had a dildo that was inserted into the wearer's vagina, and held in place by pantyhose that had been ripped in the front. It looked like she had a dick aside from the slight color difference between her skin tone and the dildo. The sex was very different, sometimes slow-motion almost and never that wild, grunting, panting violent sex that men and woman often shared.

Before the scene had ended, I had launched millions of sperm in a high arc that landed on my abdomen and I suddenly felt 20 pounds lighter. It took less than five minutes for me to fall into a restful sleep.

~

The next morning, we were sitting at the kitchen table. Mom and Dad had left for work, so it was myself, April and Brittany. In this smaller crowd, Brittany was a bit more outspoken.

"April said you almost died when a drunk crashed into you."

"I wouldn't go as far as to say almost died, but yeah I got hurt pretty bad."

"Do you have more surgeries coming up?"

"That's up to the Doctor I guess, I hope not, but if it means I can walk like a normal person..."

"There are no normal people Matt." She added immediately.

That hit pretty hard, she was right. If there were any normal people they were few and far between.

Part of me wanted to blurt out "We have something more important to talk about!" and I know I kept looking at April, waiting for her to bring it all up, but she wouldn't.

We talked a bit more, it was mostly about what was going on at their college and where they planned to spend spring break. When the conversation began to slow down, I got up and refilled my coffee mug, then told the women I was heading back to my room.

I sat on my bed, and honestly it felt like my brain decided to stop functioning completely. I could not decide what to do about Brittany, but I knew that the fact that my sister was dating a Trans woman would be something forever etched in my memory. I got up and went to my closet and began searching for a pair of kettle bells I used to use daily before getting hurt. In the back of my head, I celebrated this as the first step to me getting back to my old self and getting on with my life. I stood in front of my dresser and began controlled bicep curls, watching the reflection and making sure that my form was correct.

A knock on my door pulled my attention away and I just called out 'Come in!' the door cracked open and Brittany looked in, then looked around and opened the door further to step inside.

"Hi Matt." she said nervously.

I set the kettle bells down on the floor and turned to her.

"You two are serious about this." I said, but it was really a question.

"I thought, in case you had any questions. I should be the one to answer them."

"So, you want to lose your virginity."

She actually looked away a little and nodded.

"What will change after that happens?"

"I won't be curious, what it would be like to be with a man."

"Then why be with a woman?"

"Does it bother you that I'm with April?"

"Not at all, it's just surprising."

"If you do this, it's going to fill in some blanks I've had in my head for years. This isn't something I suddenly got curious about."

"So again, why be with a woman? You're beautiful, guys would be happy to take you out."

"Until I told them that I'm a bit different."

"Are you sure?"

"It made a difference after April told you, didn't it?"

"Yeah, it did."

"So like I said, I'll answer any questions if it'll help you make a decision."

"You have to admit, this all sounds crazy right? My sister wants me to have sex with her girlfriend."

"It's not just your sister that wants this Matt." She said, and took a nervous step forward.

Unless you've been faced with a similar situation and I don't suppose a lot of you have, then you can't understand the internal conflict. Even if Brittany had been a CIS woman, her being Trans just added another layer to things.

"Let's say I was considering this, I'd want to be clear about some things."

"Okay." She said and looked at me expectantly.

"I'm not interested in touching, or doing anything with your dick. I don't want to be mean, I don't want to seem homophobic, but it's just too much for me. If you're okay with both of us pretending that part of your anatomy is blurred out or something. Fuck, I know that sounds terrible, I'm sorry."

"It's okay, I don't want you to blow me or anything."

"Do you have some idea of how you'd want this all to go?"

"April said you've been with a lot of women, so I'd just let you do whatever you wanted."

"Whatever huh?"

"Yeah Matt, whatever you wanted." She said and took another step toward me.

"I've never been with a virgin before." I said, partially to myself and partially so Brittany would understand that I wasn't some kind of expert in introducing women to sex.

"Being a virgin is subjective, your sister and I have been sleeping together for a while. I've just never felt a man." she took another step toward me "in my mouth." and then another step and she was close enough that she could have extended her hand just a bit to touch me, "or inside me."

"And that's really what you want?"

"I do, I want to know, I want to experience it."

Her fingers reached out and rested on my shoulder and I couldn't remember when I stopped staring at her face and focused on her lips. At times, they almost seemed to quiver.

I was going to do it, of course I was. All of the chemicals in my brain processed the fact that a beautiful woman was approaching me and willing to give me anything I wanted from her sexually. You can pretend you'd act differently, but you don't get to say that unless you've been in that kind of situation.

"Okay." I said, and she took one last step. My hands automatically went to her hips and a moment later her lips were pressed against mine.

Brittany was probably 5'8" tall, but as we kissed, she seemed tiny, she felt like she had been conquered. That's not to say she simply stood there any let me explore her mouth, instead she was adapting. As my tongue rolled against hers, her tongue would become more active, as my fingers found her asscheeks and I pulled her closer to me, her hands went around my neck and when my mouth moved to her neck, she made the softest, sexiest noises that I could ever remember hearing.

When I lifted my mouth from her throat, she gasped and her breath was coming quickly. I watched her for a moment and she said 'I should tell April, just in case.'

It made sense, but I also immediately worried that any break in what we had been doing might cause me, or us, to have second thoughts and as I said earlier, there's that prehistoric connection in our brains, when sex is inevitable, humans don't want to miss that opportunity.

"We're doing this now? Today?" I asked, to be sure.

"Your parents aren't here and there's no rush, so... It's up to you."

"It's up to you Brittany." I answered.

"I'll be back in ten minutes, I promise." She said, her voice was clearly shaking and I nodded and watched as she turned and nearly darted out of my room. It had been more than a year since I last had sex and now, I'd start again by sleeping with a Trans woman. If you would have given me a million guesses, I would never have imagined this scenario actually playing out.

I heard talking in the kitchen, and then Brittany walked past my open door and went into April's room, a moment later I heard the bathroom door close.

"Hey..." April said, as she stood in my doorway.

It felt weird to even look at her, this was crazy, but it was happening.

"Hey." I said back.

She walked in, and closed my door behind her.

"I know I don't have to say this but, you better not hurt her."

"Because that's what I do with women?" I asked, a bit perturbed.

"She's special Matt, you can't imagine the kind of issues she has to deal with, this has to be something beautiful for her."

I nodded.

"She's getting ready for you, we've played around with some toys, but you still need to go slow with her, promise me."

"I promise."

"This can't change anything between you and me. I want to look at you tonight at dinner and not see you any differently."