Curious

AN: Everyone in this story is over 18 years of age. This is a work of fiction.

Curious

"Are you Trans?" She asked as she unceremoniously sat down across from me in the break room.

I couldn't even remember her name, I'd been introduced to so many people in the last three days. I'd just started working at the largest retailer in the US, I'm sure you can guess the name.

It was Missy or Michelle I thought. I remembered her red hair more than her name and I'd seen her a few times the day before. But now she was sitting across from me and I had to deal with this.

"Yes, why?" I asked, things could go in a million directions from here.

"You're pretty." She said and gave me the once over, before smiling.

"Thanks, so are you." I offered and I wasn't lying.

"So, do you like guys or girls? Or maybe both?" She asked and pulled her elbows up onto the table, and rested her chin on her joined hands.

"I'm Tracy by the way." I said, I didn't know this woman and she was just asking questions that she must not have realized were of a personal nature.

"Melissa, but everyone called me Lissa" She said and seemed very much at ease asking these questions. That was how I actually met Melissa and a week later I'd discover that when she orgasmed, it would always seem more violent if we were kissing when she came.

It's not fair for me to say that it wasn't a surprise that Lissa had never managed to keep a relationship together, her personality was almost what I would call cluelessly callous, but there was never any malice in her that I could see.

"I knew I'd enjoy fucking you." She said while staring at the ceiling of her bedroom. I lifted my mouth from one of her stiffened nipples and asked why.

"Don't be silly, it's like having a girlfriend with a dick, you know?"

We weren't girlfriends, we weren't going to become girlfriends, but I liked fucking her, clueless as she could sometimes be. She was vocal about what she liked and not embarrassed to talk about it.

"Have you ever fucked two guys at the same time?" She asked absently.

"Yes, it wasn't what I expected it would be." I shrugged, thinking back I suppose I thought sex with two guys at the same time would be ore organized, more polished, but in fact it was awkward and it's hard to suck a dick correctly when you're getting fucked at the same time.

"I like it if I'm in the mood for it, I like knowing I can make men desperate to cum." She said and I could see her mouth twisting into a wide grin.

"Do you make me desperate to cum?" I asked, because I knew this would be an interesting answer.

"It takes you a long time to cum, so maybe I'm not making you desperate but I did something right, I've wanted to fuck a Trans woman for a while now and when you showed up at work I decided I was going to fuck you."

"Right from the start?"

"I wanted to be sure first, but yeah, after I knew... Wait, is that a bad thing? You like having sex with me don't you?"

"If I didn't, I wouldn't be laying her next to you sucking on your tits now would I?"

"But you know how guys can be..."

"Am I a guy?" I asked, again, waiting for the answer that I couldn't guess at.

"You're in between I think, maybe after you get your dick turned into a pussy."

"I'm not planning on having my dick turned into a pussy Lissa."

"Don't you ever think about a man fucking you, if you had a pussy?"

"I get that know when a guy fucks me."

"But I mean, fucking you so you can orgasm."

"What if I paid all of that money, money I don't have and went through all of the pain and long time to heal, to find out that I can't orgasm anymore. It's not like could just give me my dick back right?"

"But I mean, if you want to be a woman completely."

I had stopped sucking her tits and was getting angry.

"When you asked if I was Trans, would we have started fucking if I told you I had a pussy?"

"Well, no."

"Okay, so it's a good thing I still have my dick, right?"

"I was just curious."

"Is the sex good between us?"

"Sure."

"Does it make you bi to have sex with me?" I quizzed her, because she needed to understand that I could make her uncomfortable if I had to make a point.

"I'm not sure, I mean I had a girlfriend for a month in college, but i think it was just a phase."

"Am I a phase?" I wasn't letting up.

"You're just different and that's a good thing Tracy. You don't fuck like a guy, but you feel good inside me and I like that you don't cum 30 seconds after we start. I'm not sore all over the next day after fucking you, I like that."

"You usually fuck guys that are hung like horses?"

"I just mean, sore all over, like I was in a car wreck."

"You always say the strangest things, maybe it's time for you to suck my dick before it gets chopped off if you have your way and after you get me ready, I'll fuck you hard enough to be sore tomorrow."

"Don't be mad at me." She pouted.

I took my dick in my hand and wiggled it around. "She wants your lips back on her."

She sighed and then sat up and moved down the bed till she bent and fed my soft dick into her mouth. Lissa was very good at sucking dick, she had mentioned casually that she guessed that she had been with 'at least a hundred' guys and she was 24 years old. Maybe that number just seemed like a lot to me.

I had been with a fraction of that many and that includes women too. I supposed it was easy to imagine her with a considerable body count, I couldn't imagine anyone sticking around too long with how Lissa would just suddenly say something that would have been best left unsaid.

I had turned her onto her knees and pushed her head down to rest against the mattress of her bed. Her position allowed for an unobstructed view of both her asshole and her pussy. I briefly considered fucking her ass, but that always required preparation and the last thing I wanted was to make a disgusting mess, so I sank back into Lissa's soft, hot pussy.

She wiggled her hips as mine were pressed against her ass.

"I like sex with you." She said, and I think the noise she began making was supposed to sound like a cat purring.

I thought back to the time before I had accepted who I was and tied to fake my way through life as a straight male. I dated regularly, had sex as often as the opportunities presented themselves and always preformed the way I imagined women wanted them men to fuck, physically, violently.

Lissa made new noises as my fingers dug into her hips and I slammed against her. It wasn't the way I wanted sex, but it somehow felt like I was disciplining her for being so clueless.

"Ohh, ohh, ow, ow, ungh, oh... fuuck!' She grunted as a white froth began to coat my dick as I continued to piston in and out of her.

"Ungh, Tracy, I..." She lifted her head off the mattress and I immediately pushed between her shoulder blades and pressed her head back down.

My hand left her back, and snaked around her waist and began rubbing her engorged clit. Her noises changed immediately and I kept up the violent pace of fucking her and now rubbing her clit. If I could cum again I'd welcome it and especially if I could cum before her. I wondered what Lissa would think if I just fucked her till I came and then rolled off of her and caught my breath.

Is that what she wanted? Was that what the comment about not "feeling sore" was all about? I knew I could make Lissa sore, but that was something that she was into, apparently. Not me.

It felt like this would be futile and doubt began to creep into my head, I wasn't going to be able to orgasm. So I imagined a toned, tanned male specimen, covered in tattoos and deep inside my ass, making me take all of his thick, long dick. I even played with the idea of a guy like that fucking me while I fucked Lissa, but experience had taught me that something like that almost needed choreography.

"Fuck your such a slut! Tell me you love this dick deep inside of you." I'd imagine my fantasy lover prompting.

"I fucking love it." I gasped out loud.

"Tracy, I'm cumming, please... Tracy... ungh..."

I heard her words but I was more focused on this fantasy of mine. I imagined him leaning forward and pinching my nipples hard enough to hurt, but not so hard as to beg him to stop and that triggered my second orgasm of the night, a rarity.

At that moment, it made no sense but I hated Lissa's tits and how big her nipples would get when stimulated. I hated Lissa's pussy and how good it felt wrapped around my dick. I hated how easy it was for her, life would always be easy for her, in spite of the crazy shit she would regularly say and there would never be a shortage of guys to take her to bed. I hated that she would say things that made me question my decisions and then not be able to let those words of hers quickly fade into my 'Lissa just don't realized how messed up that was' bucket.

Lissa wasn't the first woman I felt jealous of and certainly not the first time that I wished I had a vagina. But she was the first person that could so easily put me off balance. It felt like fucking her the way I just had may have had an almost therapeutic feeling for me.

I laid down behind her, and imagined her telling me she had met a guy and that we shouldn't see each other any more, then I imagined telling her that. Finally I imagined whoever of us found a guy saying she was willing to share.

It's difficult to describe, but fucking a woman always felt nice in the moment, especially if the woman I was fucking wasn't always saying awkward things, but afterward there was something much stronger than the weird feelings you get after cumming. I'd sometimes feel very insecure and depressed that they had what I wanted, they were capable of feeling someone inside of them in a way I realistically never could. I had asked a former lover once, it embarrassed me, but I wanted to look at someone who had a vagina, and have them tell me 'I feels the same, I just need lube for my ass', but she told me that the only reason she let people fuck her ass was to make herself feel like a whore. That probably took me a year to get over. There were definitely occasions I felt like a whore with a guy, but I never automatically associated anytime a guy fucked me that I should feel like a skank. Yes, it felt almost euphoric to know that I could make guys cum with my hands, mouth or ass, but women like Lissa seemed to always make me more aware of being 'in between' like she had said of me.

"I'll feel that in the morning." She said happily.

I nearly rolled over and wiped my slippery dick on her ass. Instead I let out a sigh, Lissa was never going to understand.

"Don't be mad, that was incredible." She said, giggling like she often did after sex.

I didn't have anyone but myself to blame for sticking around and fucking her, but I didn't have any other immediate prospects, and besides I might be able to seduce some guys, but unless the stars aligned, the only way I'd be getting off would be by jerking off with them, and you might be surprised to learn that just because a guy wants to fuck a woman with a dick, they don't automatically want to blow you. Oh and the 'sissygasm' or 'p-gasm' stuff? Well that might work for others, but it had never happened with me. Having sex with woman felt nice and as long as I wasn't overdoing it, or letting myself get too caught up in my regular mental insecurities, I could reasonable expect to orgasm, if things were going great, and I could keep from thinking about performance too much, then sex with women actually felt much better, but sex with men had almost always been more rewarding, I'm 'A Pleaser' apparently.

"I need to use the bathroom." I said, the little break from her was feeling more needed than it had been ten minutes ago.

"Me too!" She chirped and was up and walking behind me as I stepped into the bathroom and turned to ask why she was following and not waiting till I was finished.

"Do you stand or sit when you pee?"

"Lissa..." I sighed once again.

"I'm just curious, if I had a dick, I'd definitely stand to pee. What does it feel like?"

"It probably feels the same as when you pee, can I go please?"

"Stand?" She asked, and batted her eyelashes, like that was somehow going to convince me to do what she wanted.

"You want to watch me piss, standing?"

"I want to hold it, come on, please?"

As much as I wanted to hate it, it was actually kind of sexy to stand there with Lissa pressed up against my back, her warm, smooth flesh squeezed against me, as her arms snaked around my waist and one hand was controlling the stream while the other had two fingers extended on either side of the base of my dick, for some unknown reason.

"I'm jealous, I mean I don't want to be a guy, but if I could switch bodies for a night, I'd do it." She spoke, seeming directly into my ear.

"What would you do with your night as a guy?" I asked, this would be good.

"I'd start by fucking you, it's obvious you need some dick."

"Obvious huh?" She wasn't wrong.

"Definitely."

"You'd fuck me so I'd feel it the next day, like you enjoy?"

"Harder than that, I'd want you to tap out."

"You don't think you'd cum 30 seconds after getting your dick inside of me?"

"That wouldn't be any fun, I can tell you."

"Preaching to the choir." I answered.

"I'd fuck you first and after you surrendered and stopped being so moody, I'd fuck Angela at work. I swear that woman is a maneater, you can just tell. I bet she'd fuck me hard enough I'd feel it the next day, even if I was a guy."

"Guys feel it the next day sometimes." Well, I remembered feeling it the next day anyway.

"If you could only have sex with one person for the rest of your life, if they were REALLY good at sex, would you want a guy or a girl?"

The thing is, I'd heard plenty of what Lissa had said before from numerous people. I felt convinced nobody could say something that I hadn't already heard. It wasn't fair that I should just believe they realized my life was different than theirs, I may be more complicated or maybe not, but the biggest challenges in my life had always been gender-related and I imagined most people in the world didn't have those kinds of questions, confusions and worries.

I decided to give Lissa a taste of her own medicine.

"Well, in a perfect world I would have been born female and I'd find a handsome guy with a nice dick who knew how to use it, he'd make me happy and we'd live happily ever after. But the world isn't perfect and I like having orgasms. It's easier for me to have an orgasm having sex with women, so I'd pick a woman."

"Just so you could have orgasms?"

I studied her face, but said nothing. There, how does that feel?

"Is it fucked up that hearing that kind of turns me on?" She asked with a grin.

"What, that you're just a fleshlight to me?"

"Now that's a weird visual, me bent over with a fleshlight sticking out of my pussy."

"I like the sound of that." I said, feeling snarky.

We were back in Lissa's bed, snuggled together, and she kept teasing my dick with her fingers, clearly intent on more sex, but I knew that was unlikely.

"I really do like you Tracy, you're different."

"Ya think?"

"I'm going to be the best girlfriend you ever had." She said, oblivious that I wasn't her girlfriend, that we were just having sex. "I'm going to find a guy for you, but I want us to stay together.

"Okay." I said softly, my body had finally relaxed and it felt so nice to be pressed against her. I stopped hating her for her nice tits and hot, tight pussy. I felt her fingers moving along my arm and I felt sleep coming quickly.

It suddenly felt stupid to be so upset about things that either I couldn't change or wasn't brave enough to do.

I wanted to dream my favorite dream. Sitting on a park bench, wearing a light summer dress and feeling the breeze caress my skin. There were guys tossing a football around in the open field in front of me and I'd watch as a handsome guy wearing just a pair of black shorts and his trainers would come jogging in my direction to pick up the ball he'd failed to catch. He'd stop short, and give me a smile that would cause a new feeling between my legs, I could feel the blood rushing to my cheeks and from here it would always be different. Sometimes he'd ask to sit next to me and we'd talk, sometimes he'd walk up and extend his hand and I'd let him lead me off into the woods where I'd make him cry out as my lips sealed around his hard cock, sometimes he would take me away and we'd live happily ever after.

I wanted the dream,. and didn't care how it would end.

"Tracy..." Lissa's voice was a whisper "Are you still awake?"

"mhhmm" I answered softly.

"So what does it feel like to get kicked in the nuts?"

"I didn't even have the energy to give her one of my dramatic sighs. It may have been two minutes later, maybe two hours later, but the breeze felt wonderful and I felt the smile spread across my face as a very handsome guy in a pair of black shorts chased after a football that had strayed near me. He bent and picked it up, then watched me for a moment before offering a friendly 'Hi'

It's crazy how the most normal people in my life always seemed to be the ones in my dreams.

Maybe I'm dreaming now.