Rich Friend Ch. 01

All characters are 18 plus.

Today's a big day! I'm meeting my best friend from kindergarten, and we haven't seen each other in a long time. We've both changed a lot. Especially me. I've changed a bunch. After four years on HRT and some little changes here and there, I finally have the body I always wanted;curves in all the right places. When I walk, my long hair swishes. It wasn't easy but with all the doctor's appointments and with lots of money. I made it. Maybe a bit too much I spent there. But you know what they say, you gotta crack some eggs to make an omelet. And let me tell you, this omelet is fierce!

On the other hand, my kindergarten buddy, my best friend, Mark turned into Mr. Moneybags. It wasn't easy for him either. He took over his family's old business and made it a gold mine. Nobody thought he would do it. He used to share his ideas to make their family business better. Finally he did it. His college money really paid off! Good for him.

He did ask me to work for him but I was too busy with my transitioning. It's not like he offered me lots of money but promised he will give me a good share if the business is successful. I didn't have any cash so he asked for my labor. But you know what? I made it too. With my smile and way with words, I can charm a free drink or two at the bar. Sometimes, those drinks even turned into relationships. But they never lasted long. It was fun to fuck and buy expensive things but didn't feel real to me. I easily got bored with them and broke up. At least I have some cool memories and lots of fancy dresses from my exes. You have no idea what sugar daddies can do.

Speaking of sugar daddies, a pang of regret sometimes hits me about Robert. Now, don't get me wrong, the age difference was...well, let's just say his youngest could've been my babysitter. Awkward doesn't even begin to describe the look on his kids' faces when they found out about us. Still, the man knew his way around the bedroom. Vanilla just doesn't cut it for him. He was rough in bed. I mean It was rough for him, hehe.

At that age, fucking was luxury for him. Robert, bless his loaded soul, was more like a five-star tasting menu -- full of surprises. Only problem with him was that he was fucking old. I dated him only for money. I was in debt. I did continue dating him even after my debt was paying off though. I don't know why I did it but I did. Maybe I got used to it. Eight fucking month, I had to have sex with this gross old dude. But you know, sometimes you can't be too picky.

After paying off my debt I become a free bird. Or you can say a bitch. Broke a few innocent hearts over silly things. I just didn't want to wait and get used to it anymore. And meeting new people is fun. There's more to life than just getting free drinks and dating older guys. There's a real happily ever after out there, without needing to rely on a credit card all the time. Maybe I can finally have it all -- love, financial stability, and who knows, maybe even a hardcore fucking in the bedroom (as long as it doesn't involve toddlers calling me 'stepmom'). What the hell that would be even better. One less problem to worry about, haha.

Let's get back to Mark's topic. When Mark and I were in high-school, we were like partners in crime. We caused trouble everywhere we went in our small town. Everyone was always super pissed off with us. But that's what the kids do, right? You can't be mad at them. Or I think you can. We all have some part to play.

A few days ago Mark reached out to me after a long time. I was totally surprised. We talked a bit and it felt really good. He's a charming man now. Only If he was the one texting me. Maybe this reunion isn't just about catching up. It's a chance to be friends again like we used to be. We can make new memories, but this time without causing trouble. As long as we don't do anything too crazy, like pranks or running away in my high heels! I'll kill him if he does that. I'm a lady now, hehe.

Though Mark stopped responding to any of my messages back then, he has been creeping on my Instagram for a while. Can't blame the guy, really. Who can resist a perfectly curated feed of killer selfies? I wasn't exactly shy when it came to showcasing my confidence online. I wish I could share with you guys my id; lots of pictures with skimpy dresses. Mark never missed a single one to react to love. Maybe this reunion will be even more interesting than I thought. I'm definitely gonna bring up his creeping behavior tonight.

And speaking of creeping, my dress won't do any better for him tonight anyway. Tonight's outfit is a whole new level of sexy. This outfit shows off my curves perfectly. I'm all for embracing natural beauty. And let me tell you, I rock my B-cup with pride. A few of my friends told me to get breast implants but it never felt right to me. And honestly, today, my girls seem especially extra perky for no reason, hehe. Maybe it's the excitement, or maybe it's just a good day to be a confident woman. Whatever the reason, I can't wait to see the look on Mark's face when he sees me. Let's just hope he remembers his manners -- a lady always appreciates a compliment, even from her childhood bestie.

Oh of course, I'll talk more about my dress and my appearance today. The clock struck magic hour, and I knew it was time to unleash my secret weapon. This mint green sundress? More like a confidence missile. Tiny daisies peppered the fabric, like little green emojis winking at whoever dared to look. It was amplifying my curves. But the real MVP was the twist in the front. It was a strategic peek-a-boo situation. It was showing just enough skin to keep things interesting. Think Marilyn Monroe meets modern bombshell.

High-waisted panties? Duh. No panty lines on my watch tonight. And the shoes? Forget boring stilettos. These white heels were open-toed gladiators that snaked up my calves like a silver invitation. Each step was a silent promise, a Hello to whoever was lucky enough to see me walk by. In this dress, I wasn't just ready to meet my friend. I was ready to conquer the night. I bought this dress for just tonight's dinner with Mark. I hope Mark gives me some compliments.

But a small voice, nestled in a corner of my mind, spoke up. What will Mark really think? Back in the day, we were partners in crime, not partners in appreciating the finer points of a sexy outfit. Sure, he'd probably give me a goofy grin and a classic "damn, girl". Or he gets offended that I'm trying to flirt with him. You can't blame a girl for wearing a sexy dress. Fuck, I'm thinking too much. Everything will be alright.

The clock on the restaurant wall mocks me with its steady ticking. Ten minutes late myself, sure, but ten minutes for Mark with no sign? That's not good, not good at all. What if he doesn't show up? And here I am, strategically positioned at a cute little corner table, my mint green confidence missile practically sparkling under the dim lighting. It feels like I've prepped for a date, not a reunion with my childhood best friend. Why the fuck I'm thinking this anyway?

I feel a shiver down my back, not because it's cold, but because a guy across the room won't stop looking at me. He keeps switching his eyes between his phone and me. Then he gives me a weird smile like he wants to do something naughty in the bathroom. Ohh god, the last thing I need tonight. Where is Mark? A 27-year-old man should know the importance of punctuality, especially when faced with a bombshell like me (damn, this dress is working its magic a little too well tonight). Fuck, I'm getting wet down there. Okay, gotta cool my rocket before I explode all over the place. Now that I'm wet, this stranger's look doesn't feel bad anymore. Maybe I can take care of it myself.

Across the busy restaurant, his eyes and mine connect, like we're talking without saying a word. I'm fidgeting with my fingers on the table, feeling nervous because the person I was supposed to meet isn't here. This guy really wants me. Sitting under the bright lights, seeming as restless as me. I smirk a little at him. I grab my purse casually, making noise with my lipstick. It gets really quiet. He looks at what I'm doing, then looks back at me, looking curious. I stand up, feeling a bit wobbly, and gesture with my head toward the back of the restaurant, like I'm asking him to follow me.

The guy doesn't waste any time. He stands up smoothly, his smile matching mine, looking a bit mischievous. We walk through all the tables, and it feels like something exciting might happen. When we go past the sign for the restroom, I start to feel unsure. Maybe this isn't such a good idea. But then again, maybe it is. He probably notices I'm not sure. He must be feeling it too. "A quickie?" he says with a wink, his voice sounding deep and giving me the shivers.

There is no turning back now. With a playful nod, I push open the door, the fluorescent lights a stark contrast to the warm glow of the restaurant. The air is sterile, devoid of the background hum of conversation. We are alone. The moment stretches, pregnant with possibility. My heart hammers a frantic rhythm against my ribs. This isn't the plan, not exactly. But sometimes, the most exhilarating adventures begin in the most unexpected places. Plus I was leaking too much.

As soon as the door closes, our lips crash together like we can't wait to waste a single second to give each other a good look. It's a quick, messy kiss, but still full of feeling. His hands, strong and sure, slide down my back, urging me closer. Before I can even register the movement, he's lifting me, placing me on the cool surface of the counter. The world tilts on its axis. My high heels click against the tile floor, a forgotten detail in the whirlwind of desire.

He's close to me. His eyes intense like a storm. Showing how I feel inside. The kisses aren't soft anymore. They're strong and wanting, like we're trying hard to be close. I hold onto his hair, feeling like it's the only thing keeping me steady. His hands move down my back, making me shiver. He touches my thighs, making my skin tingle. He keeps rubbing my thighs until his hands reach my inner thigh. In that intimate moment, his fingers graze the smooth skin of my genital area.

He looks surprised for a moment like he wasn't expecting something there. I held my breath, wondering if he understood it. But then he looks curious instead. He's still really into me, which makes me feel brave. I lean closer to him, Showing him I'm okay with it. We kissed again. It feels like we're saying we trust each other. His hesitation melts away, replaced by a renewed passion that is even more intoxicating. He seems more interested in me now.

I'm leaning against the counter. Feeling its coolness on my back. He's touching me gently like he really cares. He's exploring my body slowly and carefully. It feels like we're discovering new things together like dancing. We're both getting more excited. His hand moves lower touching the lace of my panties. A jolt of electricity shoots through me. A mix of excitement and a flicker of nervousness. My breath hitches in my throat, waiting for his next move. I know what's his next move but still it's hot to think about.

He stops and looks at me. This time, he's not asking with his eyes if I like what he's doing, but if it's okay with me. Without saying anything, we understand each other. I nod slowly, and he gets it. He pulls my panties and my small penis points up proudly from her bald pubis. And it's small, no more than three inches long. I measured it a long time ago. It's getting smaller day by day. It's adorable and my need to feel his lips around it nearly overwhelms me. He's taking the scent of my pp. The smell of sweat and arousal is evident but I always use a different perfume there to make it more appealing. By looking at his face, no wonder he's hooked on it.

He reaches out and closes his hand around my pp. His hand is able to wrap completely around it, even overlapping his fingers and thumb; my pp fully disappears in his fist. He squeezes and gently moves his hand up and down, pulling my tiny balls up with each short stroke. He takes me in his mouth. With his lips pressed against my pelvis, the tip of my pp lies on the back of his tongue. He wraps his tongue around my pp and licks my shaft as he sucks.

It wasn't long, just a few minutes, before I tensed up and tried to push his head away and started moaning. I didn't want to cum in his mouth. But surprisingly he pushed his face harder into my pelvis and gripped my ass tightly with his hands. My pp pulse on his tongue as I ejaculated into his mouth, my cum filling all the space that my pp was not. He swallowed as I shot out three little eruptions of semen.

After it's over, he still refuses to let my pp go. He continues to suck me as he feels my erection deflate in his mouth. After a minute, I am totally soft. He sucks me a few times, enjoying the soft feel of my penis. And just when I'm almost convinced that he's done with my pp, he keeps continuing his art. He's sucking the life out of my pp. I don't get erection like I used to, so whatever he's trying to achieve won't work now.

My pp is over sensitive after the orgasm, so no wonder another orgasm will be right on the way if someone keeps sucking your oversensitive penis. The wave of pleasure crashes over me, leaving me breathless and trembling. My head lolls back against the cool tile, the sterile environment a stark contrast to the storm that has just raged within me. He pulls back, his face unreadable. A flicker of something crosses his features -- maybe confusion, maybe regret. But before I can decipher it, he stands abruptly, his eyes never meeting mine.

It gets really quiet. He goes to leave, looking kinda robotic. Part of me wants to say something, but I can't. I feel really exposed suddenly. The door closes softly behind him, and now I'm all by myself in the quiet bathroom. I can hear his footsteps fading away with the noise of the restaurant crowd. Though I feel weird after what happened or more like happy and sad at the same time. We had a moment, but now it's over. But hey, I feel kinda chill now. Didn't expect things to go down like that, haha.

Stepping back out into the restaurant, I sit and hope for when he'll arrive. Just as boredom starts to gnaw at the edges of my excitement, the restaurant door swings open. My head whips around, a hopeful smile blooming on my face. But it isn't Mark. Disappointment floods me, quickly replaced by a flicker of annoyance. Maybe he stood me up. The thought is ridiculous, but the longer he takes, the harder it is to silence the prickle of doubt.

Then, a voice, deep and warm, cut through the background chatter.

"There you are! Sorry I'm late," he says.

I swivel back around, a grin splitting my face wide open this time. Mark. But this isn't the Mark I remembered from high school. This Mark is... well, let's just say the years have been kind.

He'd filled out, a good kind of filled out. Gone was the scrawny teenager I used to wrestle with (though a playful part of me missed those days a little). Now, broad shoulders strained against his shirt, and well-defined biceps hinted at hidden strength. Even in a full room of people, his presence demanded attention. He towered over the seated figures, a good six feet or maybe even an inch taller.

Okay, maybe take a deep breath, Ruby. You came here to reconnect with a friend, not ogle him like a piece of eye candy. Still, a little harmless appreciation never hurt anyone, right?

"Took you long enough, stranger," I tease, pointing to the empty seat in front of me. "Did you get held up by something exciting, like a business deal with diamond smugglers?"

"I was just getting ready for our date, buddy," Mark replied, a playful smirk tugging at the corner of his lips.

I give him a fake glare. "Buddy? Who's buddy?" I pretend to be offended.

Mark looks kind of embarrassed and gives a little grin. "Sorry," he says, scratching his neck.

"Haha, I'm just messing with you," I relent, waving a dismissive hand. "You can call me buddy, haha."

He lets out a big breath, looking relieved. "Phew, I was worried for a moment. I can't call a pretty lady 'buddy', can I?"

He grabs a chair and sits across from me.

"Finally!" I exclaim, pointing to the menu with a teasing pout. "I've been waiting forever for a date with a mysterious businessman."

Mark throws his head back and laughs. A rich, genuine sound that washes over me. It's the same laugh I remember from countless sleepovers and whispered secrets, but somehow deeper, more mature.

I look at the menu, sneaking peeks at the guy sitting across from me. I feel excited about seeing him again. I wonder what tonight will bring. Maybe reminiscing about old times or starting something new. And of course, there will be lots of joking around and catching up.

"You're here alone, so are you single?" he asks, sounding playful but curious.

"That's some detective work," I say, matching his playful tone. "What else can you figure out, Sherlock Holmes?"

He looks mischievous and raises an eyebrow. "Hmm," he begins, leaning closer, "you're all dressed up, not like you would be just hanging out with a friend. I mean not this much sexy, haha." He winks. "Looks like you're trying to get someone's attention. And judging by how the guys here are staring at you, it's definitely working."

I laugh and playfully hit his arm. "Hey!" I say, "I dressed up for this nice restaurant."

Actually, I did dress up more for him, and it got Mark's attention in a way that goes beyond just being friends.

"Of course," he agrees with a chuckle, his gaze lingering on me for a beat longer than necessary. "You look amazing, Ruby."

I grin and say, "Thanks," leaning in like he did before to amplify my cleavage. I look at him, pausing for a second before asking, "So, what about my outfit, Detective? Did it catch your eye?" I watch him closely, wondering if he's more than just interested. Does he blush a little? He's looking at my cleavage. "Come on, spill it! A girl needs to know if her wardrobe choices are having the desired effect," I say, teasing him.

He laughs loudly, making me feel happy inside. "Okay, okay," he says, pretending to give up. "You caught me, detective." He looks at me with a playful twinkle in his eyes.

"So," he continues, leaning in to match my closeness, "what is the desired effect, exactly?"

I give a smile and he's amused too. "Well, detective," I say playfully, stretching out the word, "it all depends. Are you here just to catch up with your old pal from childhood, or is there maybe something more...?" I stop, leaving the question there with a little flirtiness.

"Ruby, I'm sorry," Mark interrupts, his voice laced with sincerity. I raise a hand, silencing him with a playful smile.

"Woah, woah, woah there, Mr. Serious. I was just messing with you by pointing my cleavage to you," I tease, leaning back in my chair. "Though," I add with a wink, "it seems to have had the desired effect."

A blush creeps up Mark's neck. A reaction that sends a thrill through me. Maybe this reunion is turning out to be even more interesting than I thought.

"No, seriously," he persists, his expression softening. "About cutting you off...it was a jerk move. I was so caught up in building the business. I let everything else fall by the wayside. Even the best friend I ever had."

He reaches across the table, his hand hovering hesitantly over mine. "The truth is," he confesses, his voice dropping to a low murmur, "I always regretted losing touch with you. I even used to creep on your Instagram. I did it just to see how you were doing."

I swat his hand playfully. "Creep? Sounds more like a supportive long-distance stalker to me," I counter with a laugh. "But seriously, it's okay. Water under the bridge." A mischievous glint sparks in my eyes. "Besides, at least you got to witness my Instagram glow-up in all its glory."