Bailey Ch. 01

How awkward would it be, if I had to talk to her, after walking in on her in the shower like that?

To be clear, the fact that Bailey had a penis was not enough to make me never want to talk to her again...I had somewhat of an idea as to what a transsexual was, and I certainly had no problem with any of that stuff. I was just in shock and found it pretty awkward, considering the WAY that I had learned about Bailey being trans.

I wished that she would have just told me upfront, to spare us both the trouble and embarrassment of what had happened earlier that day. After sitting in my room for a few hours after school, I decided to go ahead and meet with Bailey for the party that night...I didn't want to blow the whole thing off, because I didn't want her thinking I hated her now.

I found Bailey sitting on a bench outside of the schoolyard, around 8:30 that night. She was wearing a pair of black, skin-tight jeans, and converse sneakers, along with a black hoodie, with the hood, pulled over her head. She looked up as I approached and practically jumped out of her seat but, seemed to struggle, as she tried to find something to say to me.

"H-Hey," she stammered nervously.

"Hi..."

We were both quiet for a few seconds before Bailey began speaking...actually, it was more like she was babbling on.

"Listen, I'm so sorry about what happened earlier, I swear I can explain if you still want to be friends, please tell you still want to be friends, I really like you and I don't want to-"

"Bailey, stop!"

I held up a hand and she cut herself off mid-sentence, biting and chewing on her bottom lip, as she waited for me to say something. I paused for a moment, then laughed a little.

"I'm the one who should apologize," I said finally.

"I kind of freaked out, and ran out of there as my life depended on it...I guess that probably made it seem like I had an issue with you or something."

"You don't need to apologize; just let me explain," Bailey said.

That much, I was willing to agree to.

We sat down on the bench together, neither of us in any sort of a rush to get to the party at this point in time. Bailey went on to explain to me, that she was, in fact, a transsexual. She had begun living life as a girl at a young age, just shortly after her parents separated and divorced. She had known since she was very little though, that she was not supposed to be a boy. It was this fact that had led to her father being so angry and abusive to her.

While her mother was always very accepting of Bailey, her father wasn't open to any of it, not even a little bit.

A military man, he believed that corporal punishment and strict discipline was all that Bailey needed, to whip her into shape and make her understand that she was supposed to be a boy.

It never worked though.

Bailey had it pretty rough for a long time, and the more her father realized the beatings weren't working, the angrier he became and the angrier he became, the more beatings she received...it was a vicious cycle, until her mother decided it was time to put her foot down and put an end to it all.

"I'm sorry you had to go through all that shit," I said, as Bailey finished explaining everything to me.

"You didn't deserve any of that."

Bailey smiled and nodded. "It's okay though," she said.

"Mom moved on pretty quick, and found a better guy...he treats her the way she deserves to be treated, and he's pretty nice to me too. I'm a lot happier now that my father's gone."

"I can imagine you would be."

We were quiet for a few moments, as I tried to process everything I had learned about Bailey, in the last twenty-four hours. The silence seemed to drag on a bit too long, and I could tell Bailey was starting to get a bit anxious.

"So," she said, finally breaking the silence.

"A-Are we cool?"

"Well, yeah," I scoffed. "Why wouldn't we be cool?"

Bailey smiled, sighing in relief. "I just thought that you..."

"Wouldn't want to be friends with you anymore? Bailey, I'm not that kind of guy. I guess we all have our pasts but, it's not like you're a serial killer or something like that...you're just different...and it's not a bad thing."

She smiled again, this time with tears in her eyes and leaned forward to hug me tightly...and I hugged her back, breathing in the scent of her freshly shampooed hair...man, she smelled really good, I thought to myself. I quickly brushed that thought aside though and pulled back to smile at her. I didn't want to make any sort of a move, that could potentially damage our friendship and what we were already developing.

I cleared my throat after a moment and smirked.

"I have to say," I started.

"I'm impressed."

"With what," Bailey asked.

"Well you, uh...you've got quite a few inches down there..."

I hoped she wouldn't take it offensively since I was only joking with her...in truth, I was also a bit curious about exactly how big she was, and hoping she might be open enough to say it.

Bailey laughed, then gave me a playful shove.

"You think so?"

"Yeah," I chuckled. "H-How big is it...exactly...I-I mean if you don't mind me asking!"

Bailey chuckled, standing up in front of me now.

"Well, wouldn't you like to know?" She asked, with hands on her hips.

I blushed, as she smirked at me.

"I'm about ten inches when fully hard..."

Wow! Ten inches!?

"Ha, wow...you're actually a bit bigger than me."

"Really? How big are you?"

I blushed harder, not sure I wanted to actually give that kind of information to her but, it was only fair...I'd had the balls to ask her so it wouldn't be right for me to say no if she asked the same question in return. "I'm about seven when hard."

"Not bad," Bailey smirked. "But, I definitely got you beat."

We both laughed, and joked around a bit more about it, before picking up and making our way to the party. I was glad we had cleared the air on this matter, and that things weren't quite as awkward as I had expected them to be.

We got to the party about 9:30 or so, and it was in full swing. There was punk rock music blasting through the stereo system, typical since we were at Nick and Tyler's house after all. There was plenty of beer and liquor since their parents were out of town for the night, and the smell of weed was heavy in the air.

As soon as we arrived, Tyler greeted me and Bailey both with a beer in each hand and passed them off to us.

"Come play some beer pong with us," he yelled over the commotion.

We followed him out into the kitchen, where the pong table was set up and there was already a game in motion. After that round was over with, I and Bailey teamed up and a second round began, with us facing off against Michelle and her friend Brittany. Brittany was a gorgeous redhead, with green eyes and a set of tits to die for; she was probably at least a DD in bra size.

As the game picked up, it seemed to be tipping in favor of Brittany and Michelle, with me and Bailey on the losing side...I'd never played beer pong before though, so I wasn't exactly surprised that I was losing.

As we played, I couldn't help but notice, there seemed to be a bit of a spark going between Bailey and Brittany. We were all starting to get pretty drunk by this point, and those two just kept flirting with each other, though I thought it was just them being playful. In the end, me and Bailey both lost but, Bailey went on to challenge Brittany to another round with Tyler as her partner. They placed a bet, to...if Bailey won, then Brittany had to hook up with her upstairs.

Again, I figured it was just a joke and everyone else seemed to think the same, as they all laughed.

Brittany accepted this challenge though, and the game went on.

I only watched about half of it, before I got distracted by Nick, waving me out into the other room as if he wanted to talk.

"What's up?" I asked as I approached him.

"How you feelin, brother...you having a good time tonight?"

"Hell yeah," I laughed, as Nick gave me a pat on the back.

"That's good," he said, taking a swig of his beer.

"So, I uh...I heard you found out about Bailey?"

I blushed...had she really told him, what had happened in the showers earlier that day? "Uh, yeah...yeah, I kind of walked in on her in there."

"Yeah, the fuckin school sucks dude. They make her use the guys' shower because she was born a boy...they don't care what she identifies as."

"Can't they just have her wait until all the girls are out of the locker room, so she can use the women's room?"

"Her mom tried to get them to agree to that," Nick explained.

"The school refused. Too many other parents bitching and moaning about it, so they wouldn't budge on the matter. Anyway, I wanted to say I'm glad to see you're cool with it all...Bailey's a great girl but, she's lost a few friends over the years, because of who she is."

"I'm not going anywhere," I said, with a smile.

"You guys are my friends. Where I was going to school before, I only had a couple and they were a bit shady, to say the least...I feel right at home with all of you though, Bailey included."

"That's good to know," Nick said, patting my back again.

While Nick and I went outside to smoke a cigarette together, Bailey and Tyler must have ended up winning that second round with Brittany and Michelle. By the time I came back into the house, the game had ended and Bailey was nowhere to be found...neither was Brittany. Drunk as I was feeling at that moment, I really didn't think twice about it though.

I just grabbed another beer and went back outside to smoke another cigarette with Nick, Tyler, and Michelle.

Most of the people were clearing out now, as it was getting pretty late and the party seemed to be on the verge of ending. At this point, it was just me, Tyler, Nick and Michelle, and Bailey, who I assumed was probably passed out drunk upstairs.

I asked Tyler if I could use the bathroom at one point, and after he told me where it was, I made my way back inside and upstairs to relieve my bladder. I was just coming out of the bathroom when I heard it...it sounded like...moaning?

Drunk and curious, I followed the sound to the very last door at the end of the hallway; the master bedroom. I pushed the door open just a crack and peeked through, and was surprised at what I saw. Sitting on the edge of the mattress was Bailey, and on her knees right in front of Bailey, was Brittany. The moaning was coming from Bailey, as the other girl bobbed her head, eagerly sucking on my friends' massive ten-inch cock.

Holy shit, I thought! They had been serious...Brittany must have lost that match to Bailey and was making good on the bet they'd made together. Bailey leaned her head back and moaned louder, as Brittany continued sucking her cock and seemed to be doing a pretty good job at it too.

I couldn't help but wonder, why was I still standing here watching? Maybe I should head back downstairs, and just give them their privacy...but, I couldn't take my eyes away from them. I just stood there and kept watching, suddenly becoming aware of my own cock, which was hard as a rock now.

Was I seriously getting turned on, by this?

As Brittany stopped sucking and stood up in front of Bailey, I pushed the door open just a little more, so I could get a better look. Bailey stood up too and took Brittany by the hand, pushing her onto the bed and climbing on top of her.

Before I knew it, I was watching the two of them go at it, with Brittany's legs wrapped around Bailey's waist, and Bailey pumping her cock in and out of the girls soaking wet pussy. My hand slid down the front of my pants...I couldn't help myself. I wrapped my fingers around my shaft and started stroking, as I watched them fuck.

I snapped out of it quickly though, when a loud noise from downstairs jarred me back to reality. My hand yanked back out of my pants and I backed away from the door, quietly making my way back down to the front porch.

I sat out there with the others, continued drinking and smoking cigarettes, as my mind remained focused on what I had seen upstairs. I was still so damn turned on by it, I couldn't believe myself.

When Bailey and Brittany came downstairs finally, there was no hiding what had happened between the two of them, from the others. They were both sweaty, their cheeks flushed and their hair messy...everyone poked fun at them, and I just stood there, trying to hide the obvious outline of my erection.

Bailey and I both caught a ride home that night from Michelle, and after sneaking into my house and trying not to get caught by my father, I fell straight to sleep. I woke the following morning and found a text message on my phone; it was from Bailey.

Bailey: Wanna hang out at my place today?

I quickly typed up a response, that I would be there in about an hour or two. I needed to get a shower and something to eat, to cure this hangover I was wrestling with. I rolled out of bed and found my step-brother Mark sitting up on his mattress, staring at me with a grin. "You have fun last night?"

"Shut up," I sighed. "Don't tell dad or Jamie, please?"

"I won't tell," Mark laughed.

"As long as you take me with you to the next party you go to."

"Seriously?"

Mark was the same age as me, even went to the same school as me...we just didn't really hang out or associate while on school grounds. I certainly hadn't taken him for the party type but, then again, most people wouldn't think I was the party type either.

"I mean unless you want mom and dad too-"

"No, no, shut up! I'll take you, okay?"

Mark smiled, and we shook on it before I walked out of the room and went to shower. I didn't have much of a relationship with my step-brother, even though he was a pretty decent guy. Maybe it would be nice to actually hang out with him a little more, and develop some sort of a brotherly connection, I thought.

After showering, dressing and eating, I made my way outside and jumped on my bike, making my way towards Bailey's house. I told my dad that I'd be back that night for dinner, that I was going to hang out with my friend again. He seemed surprised to hear this. It must have been weird...he was used to me being the anti-social kid but, in the last three days alone, I had been going out and hanging with Bailey more often.

As for the previous night, he thought I had been at the movies and obviously had no clue that I had come home drunk.

I got to Bailey's and found her downstairs in the basement, playing Crash Bandicoot on the PS4. She paused the game and looked up at me as I came into the room, and I smirked.

"Feeling hungover?" I asked.

"You have no idea," she sighed, laying back on the couch.

"My head was pounding this morning...I'm not sure how I'm even alive enough to play this game right now!"

"Must be that blowjob you got from Brittany last night..."

"W-What?"

I smirked, and Bailey blushed, as I poked fun at her for what had happened. She obviously had, had no idea that I watched from the door as she and Brittany got it on together.

"You saw that?"

"I might have snuck a little peek," I admitted, and she blushed even more. "I'm a guy, what do you expect?"

"You little pervert," Bailey laughed, as she stood up and shoved me onto the couch. "Did you enjoy what you saw?"

Now, it was my turn to blush.

"Well...I didn't see a whole lot, to be honest," I lied.

"Just enough to know you were going beyond oral."

"Oh, we went way beyond oral," Bailey giggled. "That girl can suck some real cock but, her pussy is tighter than anything!"

I laughed at that. I hadn't realized how vulgar Bailey could be but, I certainly did not take any offense to it.

"I didn't even know you liked girls...are you a lesbian?"

"Not really," Bailey laughed. "I like boys more then girls but, sometimes when I'm drinking, I might get the urge for some pussy."

"And you call me a pervert."

Bailey sat down on the couch beside me and took a drink of water from a sports bottle she had sitting on the coffee table.

"What about you," she asked, looking over at me.

"What's your preference in all of this?"

"Me? I mean...girls, obviously!"

"Yeah? Ever had a girlfriend before?"

I scoffed, putting on a big grin and trying to do the whole tough guy act. "You kidding me? I've had plenty of girlfriends before!"

"Yeah right," Bailey said, as she started laughing hysterically.

I laughed too, blushing again as Bailey lightly poked fun at me for the next few minutes, about how I had no experience with girls and clearly that meant that I was a virgin. Then she brought up an interesting question...

"So, if you've never been with a girl before...have you ever considered being with a guy?"

"W-What? I mean...no," I said, rubbing the back of my head.

"Hmm? Why not?"

"Well, obviously its because I don't like guys."

"How would you know, if you've never tried?"

"Don't get all technical on me now," I laughed.

"I'm being serious," Bailey continued with a grin.

"I mean...you were watching me and Brittany get it on the other night...how did that make you feel?"

I thought back to it and I knew exactly how it had made me feel...horny as hell.

"Alright, you got me," I said.

"I guess I was a bit worked up by the end of it all."

"Really," Bailey said, sounding a bit overly excited.

"Did you get a boner?"

I couldn't resist the urge to bust out laughing at her choice phrase, "Boner," and I shook my head. Bailey put two and two together, a big grin on her face, as she playfully shoved me again. "You did, didn't you? You got a big old boner, watching me have sex with Brittany, huh?"

"Shut up!"

"Which part of it turned you on most though?"

"W-What do you mean?"

Bailey looked at me hard now, her smile turning into a more serious expression, as she stood up and crossed her arms over her chest. "Were you turned on by Brittany...or were you turned on by me?"

That was a surprisingly good question.

In truth, I hadn't really put a lot of thought into it until then. What part of that whole thing had gotten me so heated? Was it watching Brittany get fucked and suck cock...or was it watching Bailey, with those small but oh so sexy tits of hers, and that big dick, plunging in and out of Brittany's wet pussy?

I must have been quiet for a bit too long, putting too much thought into it, because Bailey cleared her throat to catch my attention again. When I looked back at her, she had the same serious expression on her face as before, as if she were waiting for me to say something. "Shut up," was all I said in the end.

Bailey giggled, shaking her head. "Alright, I won't press it," she said.

And so, we went on and started playing games together. A few rounds on Mario Cart and then we wound up playing a fighting game called Tekken together. We spent most of the afternoon playing arcade mode and versus mode, playing against one another until we both got pretty bored.

"So what now," Bailey asked, as she stood up and stretched.

"Beats me," I shrugged. "I do have to head home soon."

I glanced at the clock and it was nearly four thirty in the afternoon...I had promised my father that I would be home by dinner. "I got an idea," Bailey said suddenly.

"It's kinda cheesy though, so don't laugh at me..."

"What is it?"

Bailey hesitated for a moment, then reached into her bag and pulled out a bottle of vodka. "I brought this home from the party last night," she said, sitting down on the floor. "Wanna play a game?"

I laughed, sitting down in front of her, and contemplating it for a moment.

"What game?"

"Truth or dare...with an adult spin to it."

I laughed again. "An adult spin?"

"You can pass on whatever dare or question you're given but, if you do, you have to take a shot of this."

"I don't know," I hesitated. "I told my dad I'd be home for dinner. Plus, it's still daylight. If I come home drunk again, there's no way I'll be able to avoid getting caught."