Chapter 5: Charlie Sheppard

 

Wow, I can’t believe I’m so nervous to meet this girl. I can’t believe she’s trans. That really surprised me. I’ll admit at first I was a bit apprehensive, but that girl, Amber, what a piece of work. Kind of reminded me of my ex-fiance. She seemed very sincere at first but she looked like she really enjoyed tearing that poor girl down to pieces. I can’t stand behavior like that. Looking back at it, I can point out all the times Lexi was so cruel to other people and I just ignored it. God, she had me hoodwinked. I’m such an idiot. 

Sandra doesn’t seem anything like Lexi. She’s kind, sweet, and seems really intelligent. I just get that book smart vibe from her. Regardless of whether she’s trans or not, I wasn’t going to let that Amber girl humiliate her like that. I’ll never stand by while a bully tries to harass an innocent person. It doesn’t matter who they are. I guess that’s one good thing that came from Lexi’s betrayal. She really made me realize what really matters. 

I decide to go with a casual button-up short sleeve and khaki shorts with loafers for tonight. I hope that’s not too casual. As I finish getting ready and look at my watch to which it says 7:45 PM, I decide to make my way down to the same bar I met Sandra at. 

I find her already there waiting for me. She doesn’t see me at first as she looks around, clearly nervous. She checks her phone real fast before taking another glance around. She looks absolutely beautiful in her white short-shorts and a really beautiful tank top with flowers. She’s got strap-on sandals and one of those hair clips with flowers on it attached to her short brown hair. She looks adorable. She fidgets in her chair and takes another look at her phone and I finally decide to walk up to her. She sees me and her face instantly lights up in a smile. 

“You look beautiful,” I say. 

“Aww, thanks. You look really handsome,” she says and I give her a smile before I take a seat next to her. 

“Would you like to sit here and grab a drink before we go dance?” I ask.

“That sounds pleasant,” she says.

“Great, what’s your favorite drink so far?” I ask. 

“I really love the Tropical Pick Me ups. They’re so delicious,” she says. I order us two of those. “I’ll be honest with you, I nearly convinced myself that you weren’t going to show up.”

“Why would you do that?” I ask. 

“Because I’m trans. It’s not often that a guy like you would go for a girl like me,” she says. “I thought you only stood up for me because you were being nice.” 

“I’ll admit that was the case at first. As I said, I hate bullies. But, I really enjoyed our conversation and I would love to spend more time with you,” I say and she blushes at my words with the biggest smile forming on her beautiful face. 

“Yo, bro,” I hear Cody shout out as he walks up to us with a beautiful girl wrapped around his arm. No surprise there. His eyes go wide when he sees Sandra and a big goofy smile appears. “Aww, about time you met someone. I thought I was going to have to get you a hooker or something.” 

“Seriously Cody?” I ask. I turn to Sandra. “Meet the person I choose to share my honeymoon with. My little brother Cody. Cody this is Sandra.” 

“Nice to meet you,” he says with his typical smile. “This is Samantha.”

“Uh, it’s actually Sidney,” says the black-haired woman with breasts the size of watermelons. 

“Oh, right. Sorry, my bad,” he says. “Well, we’re going to go dance. You two should come join us.”

“We were actually about to do that ourselves. We’ll meet you over there once we finish our drinks,” I say with a nod of my head, hoping he catches the hint to scram. 

“Oh, right. Well, we’ll leave you two to your booze,” he says with another smile and a wink before he and Sidney trail off to the club. 

“Sorry about that, my brother still hasn’t grown up yet,” I say. 

She laughs. “That’s okay. He seems nice.” 

“Yeah, you could say that. He’s got a good heart, but he’s very immature,” I say. 

“I see,” she says. 

We both take a sip of our drink. It tastes like I’m drinking a slushie. Really fruity and tasty. Goes down like kool-aid. “I can see why you like these things. They really go down easy.” 

“Right? Gotta be careful with these things. I could drink them all day,” she says.

“Yeah, I’m sure that wouldn’t end well,” I say with a laugh. 

“No. Not at all,” she says. 

“So, shall we hit the dance floor?” I ask. 

She nods. “We shall.”

I hold out my arm and she wraps her hands around it as we make off to the club. It’s pretty packed as they play some dance songs. I lean in and whisper in her ear. “Don’t get too embarrassed with my poor excuse for dance moves.” 

She laughs. “Don’t worry, I’m sure they couldn’t be any worse than mine.” 

We make our way to the dance floor. Everyone seems to be bumping and grinding on each other. Cody’s practically humping the girl he just met. Although I’m not sure if that’s the same girl. I try my best not to look like a fool. Sandra on the other hand lets loose without a care. I can’t help but smile when I look at the way she starts to pull off some of the oldest dance moves in the book. She lets the sprinkler loose. I laugh as I pull out the shopping cart. We do a total retro dance-off. She goes with the cabbage patch and I show off the roger rabbit. We have a blast, laughing the entire time. I never knew I could have so much fun on the dance floor. Whenever I danced with Lexi, she’d just end up grinding her ass in my crotch, which is hot and whatnot, but it’s nowhere near as fun as this. 

Suddenly as she’s doing the funky chicken, she loses her balance and falls into my arms. We stay like that for a long moment looking into each other’s eyes. She slowly slings her arms around my shoulders and I wrap mine around her waist and we slowly start to slow dance with each other. Everything else seems to fade away as we shimmer from side to side as we take in each other. As the song ends, we separate. I take her hand in mine and lead her outside. 

“Needed a breather after that one,” I say.

She laughs. “You’re telling me.” 

“I’ve never had so much fun on a dance floor in all my life until just now,” I say.

“That’s honestly a first for me too. I skipped the dances in high school,” she says, catching her breath with a smile. 

“High school dances are overrated. I didn’t go to any of mine either. So, do you want to dance some more or…” I say.

“Or what?” she asks, looking intrigued.

“Well, we could go for a walk. I suppose the bars are probably closing. I can’t believe we were dancing for that long,” I say. 

“Yeah, time just flies when you’re having fun and I’d love to go for a walk with you,” she says. 

I smile as I stroke my thumb across the back of her hand as we stroll down the sidewalk through the empty resort. It’s dark out. For the longest time, we walk in silence. I finally decided to break it. “I had a really good time tonight.” 

“Me too! This has been the best day of my entire life,” she says with a smile. 

“You know, it doesn’t have to end,” I say.

She looks up at me with a hopeful smile. “What did you have in mind?” 

“Well, seeing how the bars are all closed, did you know they supplied my room with a full fridge of booze?” I say. 

“I did not know that,” she says, then she crooks an eyebrow. “Is this your attempt to get me back to your room?” 

“Is it working?” I say with a smile. 

She nods. “Yeah, it’s definitely working. There’s just one thing I need to know first.”

“What's that?” I ask.

“You’re not a serial killer are you?” 

“Oh god no. Blood actually makes me queasy,” I say.

“Then I would love to go back to your room with you,” she says with a smile. I return the smile and lead the way. 

We end up in my room and I search through the minifridge for something to drink. “Anything in particular in mind?” 

“Honestly, I’m not even that thirsty. Do you have water?” she asks.

“I hope so. I could use some H20,” I say. I get us both a glass of water and sit down next to her on the bed. “Soooo….”

“You know, if you want to kiss me, I wouldn’t be opposed to it,” she says. 

“Then why are we wasting time drinking water?” I ask, this gets a laugh out of her. I take her glass and put both of them on a side table. I can feel my heart thumping faster. I’m actually really nervous. I sit back down next to her and she looks up into my eyes with those lovely encapsulating brown eyes. I reach up and slide my hand up against her cheek. She leans into my touch. We inch closer together and before either of us realizes it, our lips touch. It was at that point in which we both knew, it wasn’t going to end there. 

We threw caution to the wind and attacked each other with such an intense passion. We tugged at each other’s clothes in a rushed race to get naked. As I ripped off her top, she quickly tried to cover her chest. I looked into her eyes. “Now you’re going to be bashful?” 

“I’m sorry. I… I just. I don’t really have much for boobs. I guess I’m a little self-conscious about my chest. Seeing how flat it is really gives me dysphoria. It makes me feel like a boy,” she says. 

“No offense, but it’s very apparent to me that you are not a boy. Whether you have a double D’s or not will do nothing to change that,” I say. 

Her face turns a bright red. “You really mean that?” 

“Yeah, even a blind man would see you’re a girl. It only takes a 5-minute conversation to realize that. Now stop being so bashful. I think you’re beautiful just the way you are,” I say and she reluctantly drops her hands. I lean up and kiss her. She wraps her arms around me and pulls me in. 

I tug at her shorts as I fumble to unbuckle them. She breaks our kiss. “You’re not going to be upset that I… I have a dick, are you?” 

“Are you serious? You have a dick?” I say with mock surprise. She narrows her eyes at me. I laugh. “I could give two shits about what’s in between your legs. I’m bi anyway. But even if I was straight, I still wouldn't care.”

She smiles and I kiss her as I finally get her shorts off. She lets me tug down her panties. I see a smooth service between her clenched shut legs. I spread them open and out flops a small cock. “Does it give you dysphoria?” 

“No, not as much as my flat chest. Unlike my chest, no one will know it’s there unless they cop a feel or something, but everyone notices that I don’t have boobs. You know?” she says as I slide down on the bed next to her. 

“Yeah, I get that,” I say. 

“And whenever I try on a dress that is made to show cleavage, I feel like a boy in a dress. I just don’t like my chest at all,” she says as she rolls on her side to face me. 

“I totally get that. There are parts of my body that make me feel less of a man,” I say. 

“Yeah?” she asks. 

“Yeah, like no matter how hard I work out, I still can’t get rid of my love handles,” I admit. 

She looks down and tugs at my shirt. “Why do you still have your clothes on? It’s not really fair, is it?”

I laugh and take the rest of my clothes off while she watches. “I like your love handles. They’ll give me something to hang on to.” 

I laugh as I fall back down on the bed next to her. “Thanks.”

She smiles at me, leans in, and kisses me. I pull her body against mine and she grinds her hips up to me. My hand slides down her back and grabs a hold of her ass. It’s nice and soft. I breathe her in as our lips burn together in a heat of passion. Her hand slides down and wraps around my cock. She breaks away to look up at me with pleading eyes. “Will you be gentle with me?” 

“Yeah, of course. The last thing I want to do is hurt you,” I say.

Her face flushes red. “Thanks… I only had sex with one other person and he was really rough. It hurt. Plus, you have a much bigger dick than he does.”

“Are you sure you want to do this?” I ask. 

“Yes, absolutely! Don’t get me wrong, I have stuck toys up my butt before and it felt really good. I think it was just our lack of experience,” she says. 

“Do you want to be on top?” I ask. 

“No, I'm a total bottom girl,” she says. 

I laugh. “That’s not what I meant. I mean literally. Like cowgirl style? That way you can control the pace and whatnot.” 

She smiles bashfully. “Oh, yeah, sure. That makes sense. Do you have any lube?” 

“Honestly, I did not think about that,” I say.

“Hold on just a sec,” she gets up and rushes to the bathroom, and skips back with a smile. She holds up a small bottle of Vaseline. “They always have these in most hotel bathrooms.”

“Look at that, complimentary lube,” I say as I get comfortable. She laughs and straddles my waist. 

She opens the bottle and squirts out a glob into her hand. She reaches back and smothers it up her butt. Then she gets another glob and lathers my cock as she guides it to her backdoor. She bites down on her lip as she sits down on it. I can see her face contort in pain. 

“Take it slow,” I say as I place my hands on her thighs and slowly caress her soft skin. 

“Getting… Getting it in… Is always the worst,” she huffs as my cock presses up against her tight butthole. Suddenly, her eyes go wide as it pops in and a gasp escapes her lips. “Fuck!”

“Are you okay?” I ask. She silently nods. “Just take your time. No point in hurting yourself.” 

She gives me a quick smile and slowly starts to slide her ass further down my cock. Fuck, she’s so tight. Lexi never let me do anal. This is amazing. She stops to adjust. I lean up and kiss her. She wraps her arms around my shoulders and slowly takes more of my dick. Little by little, more of my pipe slides inside of her. Finally, her ass meets my thighs as my cock gets lodged balls deep up her ass.

She kisses me with hungry lips as she holds me tightly. My hands run down her back and grab both of her ass cheeks. She slowly moves her hips up and down as she whimpers into my mouth. I pull back to look into her eyes. She bites down on her lip as her ass starts to slowly bounce on my dick. 

“Fuck that feels so good,” she moans out. 

“It doesn’t hurt, does it?” I ask. 

“Not anymore,” she says as she closes her eyes.

“Then I suppose you won’t mind if I do this,” I say as I hook my arms under her knees and flip us over so I’m on top. She holds on for dear life and laughs as she lands on her back. 

“I think I prefer it,” she says with a giggle. Slowly, I start to pump in and out of the tight death grip her ass has on my dick. 

“Just tell me if it hurts at all.”

“Thank you for being so kind and gentle,” she says with half-lidded eyes. I lean down and kiss her. She wraps her arms around my shoulders and I slowly make love to this beautiful girl underneath me. I hold her tight and kiss my way down her neck. She moans out as she runs her fingers through my hair. She brings her lips to my ear. “You can fuck me faster. It’s really starting to feel really… Really good.” 

I grant her wish and start to thrust with a little more force. Her moans become a lot louder and she grips my hair. My lips leave a trail of kisses across her skin. Our embrace molds us together as we cling to each other. I reach down and grab her hard little cock and stroke it as I thrust inside her. She cries out as my own orgasm threatens to arrive. 

“Oh my god, I’m going to cum,” I moan out.

“Cum inside me,” she screams as I lodge myself all the way inside her. I feel myself erupt as she moans out, her own girlhood starts to leak its juices. After a few more thrusts, I pull out and collapse beside her. We’re both out of breath. 

She then sits up at the end of the bed. “If you want, I can leave.” 

“Why would I want that? Do you want to leave?” 

“No, not at all,” she says, looking back at me. 

“Then why would you ask that?” 

“I’m sorry, it’s just from the only other experience I’ve had, usually shame comes after sex,” she says. 

“Well, I’m certainly not ashamed. That was by far the best experience I’ve ever had,” I say. 

Her eyes go wide with surprise. “Really? Me too!” 

“I would love it if you spent the night,” I say. “Now come here, let’s cuddle.”

Her face lights up in a color so bright, it would give the sun a run for its money. She flings herself back over and practically leaps in my arms. I hold onto her as tight as I can without hurting her as she rests her head on my chest. I look down at her to see tears falling from her eyes. “Are you crying? Is everything okay?”

“Yes, sorry. It’s just… This is the happiest I’ve ever felt,” she says. 

“Aww, that makes me happy. For a second there, I thought I did something wrong,” I say. 

She leans up and kisses me. “Thank you. You have no idea how much this all has meant to me. I’ve been in a really dark place lately and I thought I was never going to see the light.”

“Well, I’m glad I could be your lantern,” I say. 

She smiles as she looks up into my eyes. “Thanks for saving me from the dark.”