First Time for Everything

Here's a short one-shot for you, with a bit of an old school Whiskey feel to it. It's been sitting on my desktop in need of some light brushing up for a while now, I hope you all enjoy. Please keep any negative comments to yourself. If this story doesn't do it for you, move along and maybe the next one will be better.

Whiskey-

--------------------------------------------------------------------------------------------------------------------

"Fuck...fuck, yeah...s-shit, I'm g-gonna cum!"

Hearing her words drove me to thrust harder and faster, driving my cock in and out of her tight little ass, as deep as I could reach. My hand stroked up and down over her cock, jerking her off as I fucked her and finally I was rewarded with the feeling of her warm, sticky cum dripping down my fingers as she cried out and began to twitch and shake.

Her asshole squeezed and gripped my cock, as she arched her back and her eyes rolled back slightly. That was enough to throw me over the edge, and with a grunt, I rolled her over onto her stomach and buried my cock to the hilt as I started to cum, pumping my load deep into her asshole.

Once we had both finished, I pulled out and rolled off of her, collapsing onto the mattress at her side and we both lay there panting and sweating for a while.

"That was tense," Cameron finally whispered, snuggling up close to me with one arm resting over my chest. "I'm getting kinda sore now though."

"You should be," I chuckled. "That was round...what...four?"

"Something like that," she giggled, resting her head on my chest. "Then again, we both knew we'd be going at it a lot this weekend. That was the point, wasn't it?"

"Yeah, that's true."

Though the fun hadn't exactly started, until last night but Cameron had been here all weekend as we had planned...why? Because it was our six-month anniversary and we were celebrating. I didn't quite understand it, since we weren't a real couple, we were just fucking. That was the main thing we had agreed on when we first hooked up...no strings attached. But when Cameron suggested we spend the whole weekend together, I went along with it anyway.

"What do you think then," I asked, kissing her on the forehead. "Should we take a few hours to catch our breath?"

"Definitely," she chuckled, before pulling herself away from me and rolling out of bed. She stretched some, her back towards me and my eyes fixed on that perfectly shaped ass as she started walking towards the bathroom.

"If you fuck me like that one more time today, I might not be able to walk straight...and I have work tomorrow morning, so that wouldn't be good."

I laughed, watching her fat, semi-hard cock swing back and forth between her legs as she stepped into the bathroom and turned on the lights. I bit my lip, groaning as I felt my cock begin to stir again but I tried to ignore it. We need to settle down and relax for a little while, I reminded myself.

If you had told me six months ago, that I would be sleeping around with a gorgeous trans girl like Cameron, I don't know that I would have believed you. Truth was, I had always been a little bit curious but I never thought I would act on those curiosities...

I met Cameron through a mutual friend, and we clicked pretty easily with each other. Even that night, I thought she was attractive but I had no clue she was a trans girl. She was rocking the whole goth vibe, with black curly hair pulled into a bun, a choker around her neck, fishnet stockings on her legs, and a black skirt that most parents would have shit themselves if they saw their daughter trying to go out wearing.

She also had the same interest in music as me, and we wound up drinking together that night and talking about all of our favorite bands while hanging out on the balcony.

Believe it or not, though, we didn't hook up that first night.

That didn't happen until a few days later when I got a message from her online and she asked if I wanted to hang out. With nothing really going on around the house, and how well we had clicked the other night, I happily accepted and she gave me directions to her apartment.

When I got there, things started simple enough.

We had a few beers together and just sat around, talking about music and video games much like we had at the party when we first met. Somewhere into the conversation, Cameron quite randomly revealed to me that she was trans...you can imagine that I was pretty shocked.

Nothing about her would have suggested to me that Cameron was born anything other than female...but it didn't do anything to change my opinion of her. I still thought she was really cool and very attractive. After that big reveal though, things did shift between us a little bit.

Now that she had her little secret out of the way and I had seemed very accepting, Cameron turned more seductive and flirtatious. I tried to maintain our earlier conversation about one of our favorite bands, Slipknot but I could tell Cameron wasn't interested in that topic anymore.

"You know I didn't invite you over here, just so we could sit around talking about music all night, right?" She had asked me, with a grin.

When I nervously asked, what she wanted to talk about instead, Cameron asked if I had ever done anything with a guy before.

The obvious answer was no of course.

Then she asked if I had ever done anything with a girl like her before, and again, the answer was no...but I added that I wouldn't be back down if I ever had the opportunity.

And with that, she leaned in and kissed me.

That night, I had the best sex of my life and Cameron showed me things I never imagined possible with any cis-gender girl. It wouldn't be the end of our adventures together, either.

Before long, we were hanging out regularly.

Since we all had the same friends, everybody seemed pretty excited to see me and Cameron hanging out so much more often. I kept it on the down-low though, that we were sleeping together and Cameron didn't seem to have a problem with that. She would often come over to my place, which was where everybody loved to hang out in our free time.

I lived in my parent's basement, and it was almost like a little studio apartment with how it was designed. I had my own bathroom, complete with a shower and a small kitchen area. There was no stove or oven, but I made up for that with a portable stove that I had found online.

There was even a back sliding glass door, that led out into the yard and served as my own private entrance into the house. My friends would come over all the time, and we would hang out on the back patio and drink, or other times we would spend hours playing video games or just talking shit.

Cameron was one of the few in the group, that was over my place practically every other day. Nobody knew that we were having sex, or at least they didn't say anything if they did know. I was sure a few of them probably had their suspicions, but they didn't bother bringing it up to me.

I was pretty sure, my parents knew too. Or at least, Mom did.

She had met Cameron many times, and they both got along great and she knew that Cameron was trans and didn't care. She also knew though, that Cameron would sleep over quite a lot, and even though I insisted we weren't together, she would always get this big smile like she didn't believe me.

All in all, things between me and Cameron were pretty damn good...we had a great thing going for ourselves after these past six months.

There was just one small issue though...

As I lay in bed, listening to the sound of the rain outside the sliding door which was open just a few feet, and the sound of Cameron's piss hitting the water in the toilet, I started to drift off until I felt the mattress shift underneath of me and opened my eyes again. Cameron had come back from the bathroom, climbing back into bed with me, her flaccid cock swinging back and forth as she slid

towards me on her knees.

"You look exhausted," she said, with a smile.

"Hm, just sore...work's been rough lately."

She climbed on top of me and I wrapped my arms around her, pulling her in close and kissing her softly. I worked at a supermarket in the back room, unloading trucks and putting things away. It could be stressful a lot of the time, having to do a lot of heavy lifting and it took a toll on the back sometimes.

"How about a back rub?" Cameron suggested.

"Yeah?"

"Yeah, I even brought the body oil," she said, reaching over the side of the mattress to grab her purse off the floor. She picked it up and pulled out a small bottle, holding it up for me to see with a grin. "You know, you love my back rubs."

"That's true...who am I to say no," I chuckled.

"Roll over then, sexy thing!"

Cameron slid off of me so that I could slowly turn over onto my stomach and bury my face in the soft pillow. I groaned, breathing in the smell of sweat, cigarettes, and sex that stained the pillow, and felt my cock twitch between me and the fabric of the bed. Cameron popped open the bottle of body oil and climbed onto me again, squirting the oil into one hand and then rubbing it into my back.

I groaned softly, feeling the oil instantly begin to warm up and soothe my aching muscles as Cameron started massaging. "How's that feel?"

"Amazing," I said, my voice muffled by the pillow.

"You are tense," she said, working her fingers into my shoulders and then slowly moving down to the middle of my back. "You've been working your ass off lately."

"Yeah...manual labor will do that...s-sometimes," I groaned.

It's true, I was stressed with work.

Especially since my co-workers loved to fuck around, goofing off when they were supposed to be getting things done which often resulted in me having to pick up their slack. Sometimes, I felt like I was the only one working and it had been like that a lot more often, as of lately. Cameron always knew how to take the stress away though, especially when she'd massage my back like this.

She stopped after a few minutes, grabbing the oil again and applying some more, this time directly onto my back instead of into her hands. She resumed what she was doing a few seconds later, focusing mostly on the middle of my back now, and as she hummed softly to herself, I could feel her soft cock resting on one of my ass cheeks.

She worked her fingers gently into my side, and I groaned as she hit just the right spot...that's when I felt her cock give a slight twitch, and I was vaguely aware of it slowly starting to grow hard now. Cameron adjusted herself some behind me, and I felt her dick slide across my ass cheek and brush softly along my ass crack. My eyes flicked open and I began to feel a little uneasy, as she started humping me a little.

What was she doing?

I felt her spreading my cheeks a little bit, and her cock, now fully erect started sliding up and down along my crack...was this...was this another attempt, to convince me to switch things up?

That's the one little issue that I mentioned, earlier.

See, for the first couple of months that we were messing around together, Cameron seemed content with being the submissive one in the relationship. After I told her on our first night that I wasn't interested in getting fucked, she didn't bring it up again despite seeming a little disappointed.

About three months in though, she made a pass at me one night as she was sucking my dick and tried to slip me a finger.

I instantly tensed up and stopped her, and she apologized, and later we both just tried to act like it hadn't happened.

I thought everything would be okay after that but a few weeks down the line, she made a second pass. She had stayed over one night and in the morning, I was getting ready for work. I had gone to take a shower and Cameron decided to join me, something that I wasn't opposed to.

We spent a few minutes just kissing and feeling each other up under the hot water before I moved to grab a bottle of soap and she ended up behind me.

Her arms wrapped around my waist and I felt her pushing against me, her cock probing between my ass cheeks and I knew what she was trying to do, so I instantly pushed her away and might have gotten a little pissed off with her this time.

A heated disagreement followed as a result, and Cameron argued that it was ridiculous that I loved sucking her cock, but I was too afraid to let her fuck me in the ass.

I couldn't argue with that, Cameron did have a valid point but it didn't stop me from standing my ground against her.

Cameron left before I did for work, and I didn't hear from her again for the next three days straight. During the argument, she had expressed how she felt like things were too one-sided between us and that she didn't think she could commit to being strictly submissive. "I have needs too you know," she had yelled, before storming out of the house.

By the fourth day though, I was relieved when she texted me and said she was on her way over to spend a few hours together. When she arrived, I thought she would have more to add to our argument from the other day but she didn't even mention any of it.

Since then, I just assumed that she had decided to let it go but I couldn't shake the fear that it might have some sort of a negative impact on our relationship, later down the line.

If Cameron had been that upset with me that she could go three days without speaking to me, dodging my phone calls and text messages, then this must have been important...and if that were the case, how did I know she wouldn't decide to go her separate ways in the future?

The thought kept haunting me and haunting me since that last incident took place and now it was starting to play through my head again, as she continued massaging my back while gently sliding her cock back and forth between my cheeks. It was obvious, what she was trying to do.

I could have pushed her away by now if I wanted to.

I could have put a stop to this, just like I had those last couple of times but I had no idea what might happen if I did that again. Would we end up in another heated argument?

Would she suck it up, and pretend everything was fine?

I didn't want either one of those outcomes. Cameron just pushing her feelings aside seemed more than unfair, but the thought of another argument and her possibly ignoring me for another three days, wasn't a welcome one either.

And, what if it was worse this time?

What if this time, she didn't just dodge my calls and texts and instead decided to break things off with me all together?

We might not have been an official couple, but I did like Cameron and I didn't want to risk losing her completely...so, as she leaned in over me now and pressed her lips to the back of my neck, I took a deep shaky breath and exhaled slowly, trying to calm my nerves and relax.

"You okay, lover boy?"

I bit my lip hard and groaned into the pillow. "Y-Yeah...yeah, I'm good..."

She kissed my neck again, and I could feel her stiff nipples poking me in the back as she continued humping away. She shifted slightly so that the tip of her cock brushed over my puckered virgin hole and then pushed forward just a little bit, and I thought for sure that would be the moment...

Just as I expected the tip to slip right into me, Cameron stopped and pulled back, resuming her humping and teasing and I heard her moan softly in my ear. I felt her hot breath on my neck, as she started gently biting and sucking, licking and kissing, leaving a hickey just a few inches under my ear.

"Are you okay with this?"

I hadn't expected her to check with me...actually, I thought the fact that I hadn't tried to stop her just yet, would be enough to show her that I was okay this time.

Turning my face away from the pillow so she could hear me, I took a breath and nodded slowly. "Yeah," I whispered.

"Just...go slow, okay?"

I couldn't see her face from my angle, but I was sure she must have been grinning ear to ear with excitement...Cameron had wanted this since the first time we hooked up, and she was finally about to get it. I felt her pushing forward again now, applying just a little bit of pressure as the tip of her cock teased my tight hole.

Then, I gasped when I felt the head pop right past my sphincter, and my eyes went wide as my asshole began to burn and ache. Cameron gasped, right in my ear and I heard her moaning softly as she held perfectly still for a second.

"Fuck," she moaned, then laughed.

"You're so...tight!"

I was holding my breath, my asshole stinging, burning, and aching as it stretched around the head of her thick veiny shaft. She held her position to allow me to adjust, and after a few long seconds, she began pushing forward again.

I could feel every inch of her cock, the veins pulsing inside as she slid deeper into me and my hole stretched wider and wider, trying to accommodate her.

She stopped once again, with only about half of her cock inside of me now and I heard her whimpering and grunting before she licked and sucked at my earlobe for a second.

"Y-You okay?"

"I'm g-good," I replied quickly. "You're just...r-really big...bigger than I realized," I laughed a little.

"Do you want me to stop?"

"You...you've been waiting for this, for six months babe...just keep going."

"Seriously," she whispered. "I'll stop if you want me to."

"No, it's okay...keep going."

I was determined to go through with this, to let Cameron have what she had wanted for so long now. Determined to stick it out until the end, and was also hopeful that the pain wouldn't last for long and that I might end up enjoying it.

Cameron seemed reluctant to continue, but after a brief pause, she began pushing again, guiding the rest of her cock into me and stretching my hole even more.

When she finally bottomed out, she sighed heavily as my asshole squeezed around her cock and she laid on top of me without moving another inch.

As I had hoped, the pain was starting to subside a little now.

It was less of a searing, burning sensation and more of a feeling of pressure. With her buried balls deep inside of me, pressing up against my prostate, it also felt like I had to piss but at the same time, I didn't think I could go, even if I were to try.

Slowly, Cameron began moving now.

I felt her lifting herself just a little bit, pulling back some, and then gently thrusting forward again. She kept going like that for a few moments, slowly gyrating her hips, not fucking me just yet but warming us both up for what was to come.

Gradually, she began picking up the pace and she moved to pull about half of her cock from my ass.

She paused for a moment, then thrust forward and buried herself inside of me again. Grunting into the pillow, I started pulling at the sheets as Cameron continued to increase the speed of her thrusting. After a while of taking it slow and gentle, so that I could get used to the flow of things, she pulled back and I felt the tip of her cock slip from my hole.

With my hole gaping already, her cock hovered there right above it for a few seconds and I was about to ask what she was doing when Cameron suddenly slammed her entire length right back into me with one swift move.

The abrupt move took me by surprise and my eyes went wide, as I yelped and gasped, and then she pulled back until the head slipped out again, and she repeated the same action. Slamming her hips forward again, she bottomed out in one quick thrust and then kept repeating the same move over and over for about a minute or so.

Every time she would slam her hips forward, burying herself deep inside my ass, it felt like she was knocking the wind right out of my lungs. Strangely enough, though, I was starting to enjoy the feeling and my cock had even started to grow hard and was dripping with a little bit of pre-cum.

"Fuck," I groaned, pushing myself onto my hands and knees.