Wednesday, 2 May, 3:33pm
-This evening, 6pm. I will see you at the steak restaurant. The address is in the next message. John will pick you up. See you, Charlotte.
*Map with pinned address*
It's been a few days in my new sugar baby role. Alexander and I are doing well, I guess. He doesn't follow the rules of our agreement—my allowance is more than $1,000 per dinner date. He's a needy, greedy man, to say the least. I've been struggling to balance my role as a student and Alexander's companion. He wants to meet for dinner every evening, insisting it's easier to eat before heading home, because the ride is long and he hates being hungry.
Beyond just talking with him, I feel like he's "marinating" me for something more intimate. I wonder whether he's saving his desire for the perfect moment, or if he's with someone else while waiting for me to be ready.
-I'll wear the dress I bought with the shopping money you gave me. The weather is good today. I'll go to the restaurant myself and tell John to take a break. See you.
Not going to lie, the last few days—since signing the contract—have felt like a parallel universe. Instead of going to the library or taking an extracurricular class, I'm off on shopping sprees with Rita.
She's teaching me how to behave, dress, and present myself, and I'm soaking it all in. Even though I feel less anxious around Alexander after a few more dates, I still have to keep a mask on. Rita is adamant: as long as you remember it's a game, you win. Never let your sponsor see your true colours.
I reached the apartment. There is another new life update: tomorrow we're moving to a bigger rental, which Alexander prepared for me, just as he promised in the contract. He agreed to let my friend stay with me because he has no intention of seeing me at home. That apartment will be our space—no men, girls only.
Meanwhile, our current apartment is at its messiest right now. Rita is busy packing her closet into cardboard boxes, slowly going insane over the fragility of her heels and bags.
"Charlotte! Good that you came now! Help me, please! How am I supposed to pack all my shoes in this box without damaging them? Damn it, I should have kept the original boxes!"
"It's okay, you don't have to rush. John will help us with moving."
"I am extremely excited to see our place! I mean your place, Charlotte! You are growing up in front of my eyes, literally! Just a week ago, I met you at the darkest place in New York, and now you're moving us to a big, nice apartment!"
"Alexander is a caring man. I can't believe he's doing all of this just to... have sex."
"Yes, men are like this. Pussies own the world, pussies control the world and its money in it!"
Rita flung her hair and looked at her reflection in the mirror with pride.
"Just wait and see what else he will do for you once you start playing under the sheets with him...!"
"I'll help you with packing later, after my date. I should get ready. I decided to take a walk."
"If I were you, I'd never let my private driver rest! He'd be driving me just to cross the street!"
I rolled my eyes and went straight to the bathroom. Unlike Rita, I have a backpack, a few new clothes, and an envelope with cash to pack. I'm far less bothered about packing. It's true what they say: when you own nothing, you're free.
"Let me play some music for us!" I said, scrolling through Spotify on my new iPhone. It's much faster and more presentable than my old smartphone.
*Let It Happen by Tame Impala starts playing*
I don't wear makeup for school, and I never did before leaving my home. When I was younger, I used to play with my mom's makeup, but once she saw me touching her mascara, she slapped me. For a little girl it was a lesson to never touch it again. Likely, it didn't affect my mental state as much, so I grabbed my new mascara and applied a thin, one-layer-only coat to my lashes. My eyes went from being big to huge, in a good way. I felt like I could fly away on them.
Today's outfit was, of course, a newly purchased dress. Everything in my life feels brand new lately, and I like it. Not loving it like Rita does, but I'm enjoying these moments for sure. I slipped on a new Dior dress, a piece from the latest collection. It completely reflects my look, personality, and temperament: a slightly light pink, flowy dress...with a touch of dirtiness. When I tried it on in the boutique, Rita said Alexander would lose his mind over me in it, but I saw my soul. My soul was slowly introducing dirtiness into my life. Don't take it as a bad thing; it's the reality I'm living. I chose to try this lifestyle. For shoes and a clutch, I borrowed Rita's, because I can't spend money like her just yet.
"Ooooowwwww, look at her! Princess in the light, devil in the night!" said Rita while packing her things.
"You don't make me feel easier about it by constantly reminding!"
Rita went through my backpack and took an envelope —the same one I got on the first date —but now it was much fuller of cash.
"This! This should make you feel easier!"
"What if he wants to do it tonight?" My eyes filled with anxiety and my brain started the overthinking process...again.
"Then do it! Did you shave?"
"Yes..."
"Good, keep it shaved always! He must like it when it looks bald down there, no hair usually means youthfulness. Hair is for old women who don't care about their men's attention anymore."
"Rita...I'm not ready! What if I don't get lubricated and it becomes painful? Then I'll never want to have sex again!"
"Take a sex gel from the drawer in the hall, use it in case you are desert. But apply it only in the bathroom, don't let him see it! And by the way, I am scheduling a sex therapist session for you! I am done with your overthinking!"
Rita opened her phone and started searching for a therapist.
"You will be the death of me, I swear!" I said it as a joke and left the apartment.
Wednesday, 2 May, 5:01pm
I went outside much earlier, but this was exactly what I needed—a good walk with my own thoughts, plus some heel-walking practice. I'm grateful that John is available to me anytime, but after so many car rides, I need some me time—time outdoors. It's true that our brains can quickly get comfortable with good things. I'm trying to stay grounded for as long as I can. I'm not judging Rita or other sugar babies—maybe they're swimming in their own sea—but I don't feel like I fully belong to this.
I turned on some music, put in my headphones, and started my golden hour walk to the meeting point.
*Hypnotic by Zella Day starts playing*
New York is charming when the sun, with its orange highlights, shines on the concrete jungle. Dull, grey buildings become playful, their designs seeming to bounce back to a time when people actually cared about originality. Yes, I'm referencing history again. Abandoning my hobby and potential career feels incredibly sad, but without money I can't pursue it. So, it's not goodbye—just "see you later."
As I walked, I couldn't help but notice the eyes on me. Men of all kinds and ages were either glaring or staring. The walk started feeling less relaxing and more like astronaut training: intense, especially mentally. I don't know why—I imagined an astronaut, but they surely have an intense training program, not just a physical one. I tried to turn my shame and shyness against themselves and fight back with fake confidence. I thought about Rita and her skills...and myself, just a girl I was a week ago. This is such a big change; I deserve the looks and stares.
After about twenty minutes, I felt almost no anxiety at all. Songs in my playlist changed from one to another, boosting my confidence. I saw Alexander's building ahead of me and wanted to stop for a moment. I looked around and saw many people, all in formal attire and focused on their own tasks. Do any of them know Alexander owns this place? And even more, do they know I'm seeing him?
I turned to the main entrance and looked at it one more time, reminiscing about my first date with him. Still, my brain would play games with me and give me those same intense emotions about something that happened so recently, just by looking or thinking about it.
While daydreaming, I saw a man coming out of the main entrance. Was my mind glitching, or was he really walking in slow motion? He saw me almost immediately and walked straight toward me. In his eyes, I could read that he had something to say, but at the same time, he was on the phone with someone. I tried my best to keep it casual, but anxiety was already starting to spiral.
"Excuse me, are you the model for our AI photoshoot?"
"Sorry...I don't think I understand what you're talking about..?"
"We're looking for the model who was invited to be an ambassador for our new AI software... We've been looking for you for almost an hour!"
"I'm sorry...what AI? You must be mistaking me for someone else, I'm just standing here."
I heard someone say "All set" through his phone speaker, and his face went from relaxed to red. I saw a man blushing in front of me. He ended the phone call.
"Miss, my apologies! I mistook you for a model that my company is looking for. We're wrapping up preparations to launch a new product, but the model we arranged is very late, so I went outside to find her in case she got lost! I'm genuinely sorry I confused you!"
I was shocked. Whether it's the power of the dress or the power of my mental work on the walk here, I just got mistaken for a model!?
"It's okay, likely you didn't scare me or waste my time...yet." I smiled at him.
This man isn't old, to be fair. I think he's slightly older than Rita, which makes him a very young man compared to Alexander. He smelled like expensive cologne that lingered on his white shirt and elegantly cut pants. He had a well-trimmed beard, which only highlighted his green eyes.He looked at me for a few more seconds and said:
"May I know your name? If you don't mind, let's introduce ourselves and start this conversation over again?"
"I'm Charlotte."
"Nice to meet you, I'm Riven. Ten times sorry again about what happened. You are so beautiful—I'm sure you've been mistaken for a model before..."
"You're the first one..." I blushed.
These words sounded much sweeter and more intense than anything Rita or Alexander ever said. His words actually tickled something in my brain.
"Well, I can't be sure about that, but...I'm definitely not the one who is about to ask for your number today..?"
"Riven...I...I have dinner with my friend now, I should go..."
Friend? Do friends dress up like this for dinner? I hope he believes me.
"I'm not asking you to spend the evening with me today, but I would be delighted to get to know you better sometime in the future..."
My heartbeat increased. I want to know him too. His presence makes me nervous in a way I've never felt before, but my contract... There's no mention about "being friends," so I don't think it's criminal to give him my phone number. Also, I'll use a personal SIM card for this.
"Sure, take a note..."
I spelled the number out for him and glanced at his shaky hands. Oh my God. He's into me...!
"Got it! Thank you for your time, Charlotte. I should get back to work as well. Enjoy your dinner with a friend!"
"Thank you, Riven. Goodbye!"
"See you soon!"
He walked back toward Alexander's building. I followed him with my eyes, not blinking once.What an evening. I should rush to meet Alexander—he must be at the restaurant already!
Wednesday, 2 May, 7:45 pm
This evening, I was energetic and joyful. I think Alexander noticed, because I was more chatty than before.
"I can feel you're starting to open up to me, Charlotte."
He put his arm on my thigh. We sat in a booth, so this time our bodies were closer than before, instead of keeping a formal distance.
"Maybe you're right... You're doing so much for me and my friend. I wouldn't feel so uplifted if there was no Alexander in my life..."
We both smiled at each other. He squeezed my thigh a little, then slowly moved his hand away. I was worried he'd feel the tremors coming from inside me, but thoughts of Riven helped me hide it. I was, in fact, more open today. I'm glad that thinking about a new guy I met made Alexander think my mood and thoughts were dedicated to him.
"Are you excited to be in your new place tomorrow?"
"Of course!"
"You'll be even closer to me, and apart from that, there are plenty of stores for you to shop at in your free time. Remember to spend the allowance I give you—like on the dress you're wearing today. Spending money looks good on you."
Oh, he's a devil...or not? Rich men are strange; he gets excited when I spend his money. What level of wealth starts to warp your mind? What does it take to become like him?
"Thank you, Alexander. I'm saving for college, actually. You know that..." I said, letting a bit of seriousness show on my face.
"Don't be so strict with yourself. You deserve nice things in life. Speaking of which, I want you to try something tonight..."
So tonight is the night. Will I lose my virginity to him...? I don't think he's talking about anything but sex. I could see him growing less and less patient. The Dior dress became a catalyst—he couldn't wait any longer.
"After tonight, Charlotte, you'll be able to invest in your degree. You know how I feel about you. I'm willing to give you more allowance, since it's your first time. I'll be gentle with you."
I didn't say anything back. I just looked at him, trying to prepare myself for a tough night.He signaled the waiter to bring the bill; we were ready to leave the restaurant.
"I need to be home not too late, I have school tomorrow..."
"Of course. John will drive you back safely after we finish."
Finish... That word has a different meaning in my head—a dirty one. How does Rita deal with conversations like this? I needed her presence and support badly right now.
Alexander has his own drivers; John is assigned only to me. We got into the car and headed for an unknown location. He took my hand almost immediately after we sat down.
"I have a surprise for you... Have you ever stayed in a hotel before?"
"No, only motels on highways..."
"Well, tonight you'll be staying at a five-star hotel, in a presidential suite. All for you, my diamond."
Nice... presidential suite. I need to add that phrase to my sugar baby vocabulary.
"Has any president stayed there before?"
"Haha, maybe. This room is for anyone who can afford it. If you have ten grand to spend on a room, it's yours."
"Oh wow..."
I was excited to see the hotel and the room, not to mention saying goodbye to being a virgin.I never thought of my virginity as something special; I never really thought about it at all. Sex was never a theme of interest for me, so I always told myself that if I met the right guy, I'd do it with him. But life had different plans, and tonight I'll be selling it to a man. An old man.
We arrived at the Four Seasons hotel. The place looked absolutely stunning—more like a contemporary art museum. The lobby was crowded, so no one really paid attention to Alexander walking with me, holding my waist tightly. He looked proud, like a predator showing off his prize, while I tried my best to detach from the moment.
The room was already prepared for us, and his assistant had checked him in for a smooth, fast experience.
Alexander opened the door and let me go inside first. The suite was like a modern-day castle: floor-to-ceiling windows opening up views of New York, a minimalist yet posh interior, and a big bed. With each step inside, I discovered new angles—there was a dressing room, a spacious open shower, and a jacuzzi. The whole space had a smell of rich wood and green tea, giving it an extra touch of chic.
I heard Alexander closing the door. He went straight to the window and stood in front of it, observing New York from a bird's eye view.
"How do you find it?" he asked, not turning to see my reaction.
"It is...so big. I never dreamed of staying here! The smell in the room is nice and..."
"And the bed is California king..." he finished my sentence, even though I didn't mean to say that.
He turned to me and slowly walked over.
"I'll go take a shower now. If you want to join me, you're more than welcome. If you're not ready yet, you can shower afterwards. I want to be fully prepared when I see you fresh out of the shower with just a towel on..."
Alexander leaned in to kiss me. It was so unexpected as I didn't have time to react or process it, so I just went with the flow. I slowly followed his lips' motion. He's a good kisser, but I'm just not attracted to him enough to truly enjoy it. I needed to do something, and fast...
Riven! He quickly appeared in my mind—his look when I saw him walking out of the building. His height, his eyes, his smile...his broad shoulders. He became my remedy in this intimate moment with Alexander. I felt myself becoming excited. Within less than ten seconds, I caught my lips leading his, not vice versa.
"Charlotte, your lips are like honey. Peaches dipped in honey..." he whispered to me.
"I'll be waiting for you from the shower. Don't be late..." I replied, slowly pushing myself away from him. He couldn't stop smiling.
While Alexander was in the shower, I decided not to waste time and went straight to my phone to text Rita.
-Rita SOS, I am about to do it!
-Let that green leaf fall down! Go go go!
-Are you wet, Charlotte? (Why do I sound like a pervert lol)
-Not sure
-OMG, you nasty girl!
-talk later. bye.
When I was about to hit "do not disturb" button, I saw a message from an unknown number:
-Nice to meet you, Charlotte. This evening I will remember for a long time :).
RIVEN! That's him! If only he knew how I almost started taking off Alexander's shirt while imagining it was him...
-Me too
Why am I feeling some kind of rush in my body? Why do I reply like this to him, with such a straightforward flirt?
I put my phone away. The sounds of shower stopped; I assume Alexander was ready. So it was my turn...I decided to surprise him by getting undressed right in the main room. It felt like a computer game where someone else was controlling me. I didn't want to undress, but something told me to.
Alexander came out of the shower and saw me standing naked in the room. He didn't say anything, just walked slowly to the bed, purposely dropping his towel from his hip line.I saw it. I saw an older man's...dick. I'd seen male private parts before, when my classmates would collectively watch porn in the school bathroom, but the penises were...young. Alexander's, on the other hand, was different.
I didn't show any reaction on my face, but inside I felt nothing, too. I felt my body going numb. I couldn't run away; I had to finish what I started. I went all in to face my current biggest fear—I went straight into the hands of a predator, who was staring at me, ready to take a bite.
There was no pre-intimacy shower; Alexander accepted me in his arms and flipped my body on the bed. Without realizing it, I was lying on a bed that felt like a cloud, with a powerful, extremely rich man on top of me. I closed my eyes and imagined my meeting with Riven, our short but memorable conversation.
My mind went deeper than just remembering him. I started fantasizing about him. Hoping this would not happen, but unfortunately my dreams were shattered quickly. I opened my eyes and saw Alexander on top of me, catching his breath to find a comfortable position to start intercourse.
"I'll do it slowly tonight..." he said, without much care compared to our previous dates.
Riven had completely disappeared from my imagination. My body went into fight-or-flight mode.
He started kissing my neck, which felt incredibly nice. Honestly, it felt better than kissing him, because I didn't have to see his face in front of me or feel his breath between each kiss or tongue twist. Then he whispered:
"My little diamond..."
His sword went halfway inside me. I could feel my protective layer fighting not to let him in.I almost screamed—it felt like trying to do a full split without any stretching or experience in gymnastics.
"Alexander, please...go slowly."
I started losing my breath. Sharp pain started taking control, and I found it harder to concentrate on sex, kissing, or even the reward money. Riven was long gone from my mind by then. The pain became unbearable.
"Pain will soon switch to pleasure..." he whispered, while his voice thick with desire, and pushed what was already half way inside even further. It went all in.
I started crying. At this point in our "sex" all I could think of was pain. He stretched my uterus without any care or slower motion, despite his promise.
"You look so hot when you're crying..." he continued, having sex with me without my full presence in the moment.
I could hear his groaning and slight moaning, but I couldn't say a word. I was just trying to keep up with the pain. Alexander is definitely not the owner of a big penis, but it was more than enough for the first time.
Suddenly, he moaned much louder ,
"Oh my gosh...I'm close..." , as he quickly pulled it out of me, flashing bright red blood covering his wrinkly dick.
Alexander insisted on not using any protection, which I thought made sense because I was his...by contract. My purity didn't need to be proven, while he was doing frequent STD checks.
I felt instant relief, but seeing my blood was terrifying. He was pleasuring himself while keeping eye contact with me, when suddenly I saw him releasing semen from the little hole in his penis. The tip looked like a mushroom, which would have made me laugh under different circumstances, but not now. I was too damaged to look at the situation with any ease or humor.His semen went on my stomach, which felt like warm, thick cake icing.
"Welcome to adulthood..." he said, barely catching his breath. "You are a real woman now..."
I didn't say anything, just cried my soul out. In that moment, I realized how wrong it was for me to have sex with him. My body wasn't warmed up; his touch and kisses didn't please me at all. I felt disgusted with myself as I continued to lie on a messy bed with blood and Alexander's fluids on my body. The bed didn't feel like a cloud anymore; it went from feather-soft to cold and sharp stone.
Alexander handed me a box of tissues and told me to clean myself up.
"I don't want you to cry, Charlotte. It's not the end of the world. You were amazing."
"Don't come closer to me! You promised! You promised to be slow and gentle!" I screamed through my tears, not realizing how harsh I sounded.
"Don't ever say like that! I did nothing wrong! "
I saw Alexander's growing rage. He went from nice to aggressive in a span of a few seconds. Tats made me stop crying; I suddenly felt tiny and powerless.
"It is giving me so much pain! What did you want me to do? I asked you to go slower, but you just sped up! You were hitting the wall of my..."
"So I'm big for you, isn't it?
Alexander softened and started smiling. He didn't let me finish my sentence and leaned in to kiss my forehead.
"Please take a shower and get ready to be sent home. I'll tell John to stand by".
He never misses a second in his life; everything is well planned. I wondered if our sex was planned too, from the moment he kissed my neck to the culmination. Forcing myself, I went to take a shower. I turned the water as hot as possible. I wanted to boil my skin instead of feeling pain and shame. I couldn't stand straight either— the pain between my legs was so sharp.
Wednesday, 2 May, 11:05pm
Alexander waited patiently for me to get out of the shower. Once he saw me, standing like a homeless kitten in front of him, radiating an intense steam from my body after a hell shower, he said:
"Thank you for the evening, you are exceptional. I know you didn't enjoy today as much as I did, but I hope I will make you feel better with our next tries...and this..."
He placed an envelope, this time it was from the Four Seasons hotel where we were now, filled to the brim with cash. It was so packed that it was impossible to close one part of the paper with another.
"Here is ten thousand dollars, Charlotte. I know you are terrified now, but once your beautiful flower heals, you will be open to enjoy a world of pleasure with me. I have to go."
"Thank you," I said and waited for him to leave the room first. I didn't want him to see me naked again today.
Within less than an hour after Alexander left, I was reaching home. This ride was silent; neither John nor I talked. One hand was touching my lower stomach, while the other held the envelope tightly. Money felt like a therapist to my pain, reducing it with each minute. He gave twice as much as written in our agreement, breaking rule one more time again.
I went upstairs and opened the door. Rita didn't work today, as she was exhausted from packing. When I came home, she was sleeping on a bed. She heard my steps as I walked into the bedroom, causing her to wake up.
"How was your evening?" she mumbled while fighting her sleeping state.
I quickly got undressed and lay on the bed near her.
"Please hug me, Rita."
"What happened?"
"Nothing. I just want you to hug me..."
Rita put her arm on top of me, without asking any more questions. The rest of the night, we spent in silence.