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Senior Year Fun Ch. 02

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Previously: I just fucked the guy next door. I think he’s hot, but I also think I’m getting feelings.

I wonder what he will think when he finds out what I’m really into… and how many people have fallen for me just the way that he is now.

I walk back in the room and slide back into bed. Ryan looks so cute sleeping on his stomach with his dark hair a mess. I run my fingers through his hair and down his back. After a couple minutes, he finally wakes up and smiles at me.

“We fucked without a condom and I was too drunk and excited to even think about it…”

Well those are not the first words I like to hear after a fun night. “Good morning to you too. I have an IUD, so I definitely won’t get pregnant. I get tested every few months just in case.”

He lets out a sigh of relief. “Oh thank god. Caroline is the only person I’ve slept with in months and she refuses to let me fuck without a condom. I was just so ready to fuck you. I didn’t even think about it.”

“It’s fine. I hate condoms. I don’t plan on ever using one with you… but I do need to tell you something first.”

His face looks a little worried. Before he can speak, I continue, “It’s not bad. I don’t think, at least. Maybe we can go get some breakfast and talk?”

“I would love that. Let me go brush my teeth and change. I’ll be back in a few.”

He throws on his clothes and goes over to his place. I get changed and go sit on the couch next to Jess, who already is drinking coffee and watching E! News.

“Jess. We fucked. And it was amazing!”

“So I heard… through the wall last night.”

“Oh yeah, sorry about that… maybe I should have gotten a two bedroom so you could stay here in your own bed.” Jess is the kind of person who floats through life and good things happen to her. Partly because her parents have old properties that make them millions, so she doesn’t have to worry about money. But she’s just outgoing and much more social than I am. But we understand each other and have no secrets.

“Actually, I already told my parents that I love this place and they’re talking to the leasing manager to find me one in this building. Hopefully right above you so we can be neighbors and I can look out over the pool too!” She is also not afraid to use her parents’ money. It used to bother me, but now that I’m used to it and know her better, I know she just wants to enjoy life and if using her parents’ money is the solution, she will use it.

“That is awesome!!!! Although I’m not sure I want to help you carry boxes up to the third floor… I struggled just getting to the second floor.”

“Ali, please. I’ll hire people to do that. And if they’re hot, I’ll tip them with sexual pleasures.”

“Oh God, Jess don’t say it like that. Now it’s just creepy!”

We laugh for a moment and my face goes serious. “What is it?”

I take a deep breath before saying, “I’m going to tell Ryan.” Her eyes open real wide and her eyebrows shoot up. Oh no.

“WHAT?! You’ve known him for a total of 50 hours. So he gave you some orgasms, but that doesn’t mean he needs to know everything!”

I knew this would be her reaction. “I know, I know. But I kinda like him. And his dick. And I’m kind of in a commitment, ya know. I can’t just drop everything and be his.”

Jess’s pouted lips and wondering eyes show me that she’s trying to think of something. “How about you just wait. What if he goes and tells everyone?”

“Well then I will go back to living my life and act like the boys across the hall know nothing.”

She knows that I’m going to win this. “Okay fine. But if this backfires… I told you so.”

“I get it. We’re going to breakfast and I’ll tell him there.”

Now her eyebrows are even higher… how does that not hurt? “You’re telling him in public?!”

I get up and grab my stuff, leaving her shocked on the couch. “Oh by the way, this sparkly blue key up here is your copy! Love ya!” and with that I leave.

Ryan and I go to a cute little diner that my dad takes me to when he visits. If my dad knew about my hobbies, he would freak out.

We order and he’s looking at me with those perfect eyes. This isn’t normal for me. I don’t go on cute little dates and hope the boy likes me.

“So. I have some explaining to do.” Now his face looks a little worried as he sips his water. I continue on, “I don’t really have relationships. Not assuming this will be a serious relationship… but the last one I had was a couple years ago. The guy, Max, was horrible. He was with me for my dad’s football tickets. My gymnastics coach never let the team have fun, so the only time I ever saw him was when my dad was taking us for an appearance or game. I finally broke up with him. Then I quit the gymnastics team and my life became interesting…”

I explained my dad’s job and how he’s basically rich for analyzing football and making money for the team. I try not to live off of my parents’ money, so I have a job, just not a normal job.

Here comes his first question, “So how did your life become interesting?”

“Well, I started Kartal Escort going out. I was taking 2 summer classes and if I wasn’t in class or studying, I was drinking and partying. I met one of my dad’s coworkers, Joey, at a fancy rich people party. He was a NFL player and had more money than one person needs. So we became friends and then fuck buddies. He introduced me to a world I didn’t know existed.”

Ryan is so interested in my story. He’s nodding along and asking clarifying questions to keep things straight. I don’t feel too shitty about myself yet.

“So one night he takes me to dinner and takes me shopping. He buys me this tiny lingerie set and a sexy dress. He told me we’re going to a lingerie party and wants me to wear them. Of course I go with him and when we get there, I realize that it’s way more than just that.

We walk in and grab champagne. My heels clicked on the marble as we mingled with the other guests and drank more. After a few more glasses, he asks me to be open-minded about something. I was a little tipsy and so turned on, so I went with it. We go upstairs and he unlocks a door to a dimly-lit room with a massive bed.”

The waiter serves our food and I’m not sure I should continue with this story…

Ryan interrupts my doubtful thoughts, “So… continue this story please.”

Okay fine. I continue on, “He lays me face-down on the bed, ties up my wrists and ankles, and is fucking me. The room got darker and he was spanking me and pulling my hair. I don’t think I stopped cumming the whole time. Then I hear people talking and realize they’re in the room. They’re leaving money and asking who is allowed next.”

Ryan’s face is covered in disbelief, but I’m this far in so I might as well keep going.

“He explains to me that I can have whatever I want. These people pay to use me and watch me. I was tipsy and so turned on that I let them do as they wanted to me. And then I made a career out of it. But that’s a long story. So now, here we are… do you still want to go home and fuck me?” I say the last sentence with a sassy smile, hoping he thinks it’s cute enough to ignore all the fucked up debauchery I just let out.

The questions come pouring in. “So your dad doesn’t know about you and this guy? Or your job thing?”

“Nope and nope”

“And you just let people fuck you?”

“It’s not always that. I get to pick and choose. Some people love being teased. Others just want to watch. It varies based on person.”

He asks this one with extra curiosity. “So do you still fuck that football player?”

“Not really. My dad almost caught us and he thought it was too risky. He didn’t want there to be tension at work. Which I understand. I wasn’t in love with him or anything, so it wasn’t that big of a loss.”

“Have you ever been in love?”

Wasn’t expecting that question… “Um, I don’t think so. Max was my only relationship, which was barely even that. Joey was more of a dominant relationship once we got into that world.”

His mind is wondering, I can see it in his eyes. “I don’t know about this.”

Shit. I ruined it. “Okay, I understand. I know it’s a lot to take in.”

“It might take me a while to get used to it, and I want to know who you’re with and where you’re at, but I just can’t let you get away from me now. Not yet.”

Am I hearing things? Is he implying that he wants to be with me? Even though I’m basically an expensive sex toy?

“Wait, so you’re saying you still want to fuck me?”

“Yes. Well… yes and no. I want to date you. You can’t tell me that last night wasn’t different for you.” His face immediately shifts into a shy, doubtful expression.

He’s right. I’ve never been fucked and wanted more than just the sexual relationship. I’ve always wanted orgasms… and money. It’s hard to stop. You get addicted to it.

“Yes, last night was different. I didn’t want to say anything and seem crazy. But I guess I threw the crazy thing out there with this whole sex job story.”

He laughs and I feel so much better. He doesn’t think I’m some weirdo. Maybe this will work.

He tells me about his internship with some financial company downtown and how he can’t wait to graduate and have an adult job. He wants to work in corporate America, make it big, and live the perfect life. I can’t judge him for that. My dream was to become a doctor, marry a hot doctor, and have smart doctor kids. Not exactly like that, but you get the point. Once I got into BDSM and experienced the thrill of it, I’m not sure that my dream is still my dream.

After breakfast, he heads to his internship to get some work done before the work week actually starts and I go home to tell Jess that maybe, just maybe, this could be different.

Later that day I’m at the gym and get a text from Lucas, one of my dominants, or as Jess and I call them “masters” or “clients.” Sometimes if we’re around people who know that I’m trying to become a doctor, we call them “patients.”

Lucas: Hey Ali baby. I know we usually meet on Sundays but I’m going to have to reschedule. Yakacık Escort I will still send you $1,000 today if you can meet later this week.

Shit. Ryan made me completely forget about my only consistent master right now. I never forget about this type of thing. I mean this is my job. And Lucas is a little more than just another master. He’s a doctor and pulls strings for me to shadow and volunteer at his clinic. He also pays me $1,000 a week to go on a date and maybe fuck him. And he’s not bad looking for a 38-year-old.

Ali: Hey babe. I don’t have much planned for this week. Whenever you’re free, I’ll be waiting for you. Xoxo

One of the reasons I love this “job” is because I can focus my time on school. I fuck a couple guys every so often… it relieves some stress and I make money from it. It’s really not a bad deal.

Ryan said he was going to try to get used to it. He doesn’t know all the details about my job either though. Would he be okay with me dating and fucking other men regularly? I’m not sure about this either…

Lucas: Would Tuesday work for you? I’m working a half day. I can take you to lunch and we can spend the afternoon at the spa before we head to my place.

He is too good to me. He knows exactly what I like and other than paying me weekly, he buys me clothes, takes me out nice places… it’s great. I guess he’s like a sugar daddy, but I don’t like being called a sugar baby. I think of myself more as an expensive date with benefits.

Ali: That sounds perfect. I’ll send you the address to my new place if you want to pick me up. I’ll make sure to look extra cute for you.

I still like to flirt with them. It’s part of the job, right?

Lucas and I finish our text conversation about Tuesday’s plans. Should I go ahead and tell Ryan? I’ll wait until we see each other again instead of texting him right now.

I run a few more sprints, do some ab workouts, and head for the sauna. I sit and meditate for a few minutes. I would totally fuck in the sauna. I should definitely make that happen soon.

Once I’m home and showered, I grab a book and head for the balcony. Someone nearby is grilling and it smells delicious. Someone else is still playing music by the pool. The surroundings are very college-like and I love it.

My phone dings and I see a notification from my “job” app.

YES SIR: You have 1 new message.

I open the message and see an average-looking profile picture. His name is Tim. He’s 45 and is wondering if I can meet tonight or tomorrow. Typically I would say no on a Sunday because it’s my day with Lucas, but since that’s rescheduled, the only thing holding me back is Ryan. I guess I should talk to him.

I respond to Tim’s message that I will give him an answer in about 30 minutes. That way it limits my conversation with Ryan and I can get ready for our “date” by dinnertime.

I go over and find Ryan at his desk in his room. He’s wearing simple khakis and a polo shirt, but he looks so cute in it.

“Hey Ryan. Are you busy?”

“Ali! No, of course not. What’s up?”

“So… ya know how I was telling you about my job? And how I meet with people every so often?”

His face is just… blank. “Yeah…”

“Well I usually meet with Lucas on Sundays, but we’re meeting Tuesday this week. But someone else wanted to meet tonight. I just wanted your opinion on it. This kinda is my job, so I can quit… but I’ll need longer than a 2 weeks notice. It’s hard to explain. I just –“

He holds his hand up to stop me. “Ali. We’ve known each other for a weekend. Not even. Don’t let me interfere with your life. Or love life. Whatever it is.”

“Are you sure?”

“Yes. You’ll have to shower or something before you get in bed with me… but other than that, just be safe.”

Ugh, he’s so perfect.

I go and straddle him in his desk chair, running my fingers through his dark hair.

“I’m not sure what time I’ll be back. But I want to see you tonight.”

“Just text me. I’ll be here all night working until I leave in the morning for my internship.”

He gives me a kiss and squeezes my butt. I grind down on him a little in response before going home and getting ready.

I already showered after the gym, so I just need to do my hair and makeup. I go for some natural makeup… I’m feeling lazy but also don’t really care if he thinks I’m that attractive. After sliding on a light pink bodycon dress and black strappy heels, I’m ready for Tim to pick me up.

After getting a text that he’s here, I text Jess to let her know I’m leaving. We have our locations tracking each other at all times, just in case.

I go downstairs and Tim is waiting in a white convertible BMW. I don’t know much about cars, but this looks nice. Also, good thing I didn’t try too hard on my hair since we’re riding top down.

We head to a fancy bar/restaurant downtown called “Indigo.” We walk in and the lights are all shades of blue and tables are all large, round booths. Tim lets me slide in the booth and watches my breasts as I lower into the seat. Kadıköy Escort He slides in next to me and hands me a drink menu.

After some small talk, I order a French 75 cocktail and get to studying his face.

Once you’ve been dealing with men in this business, you learn the cues of what they like before even getting in the bedroom.

Tim has short, blondish-brown hair. His eyes are brown and he has light stubble down his cheeks. There’s nothing that makes him super attractive, but he is definitely not bad looking. From what I can see under his button down and slacks, his body can’t be too bad.

He definitely looks like the kind that wants vanilla sex and thinks that handcuffs are kinky. I really hope he proves me wrong because I’m going to need a lot more than vanilla sex for this to be worth $3,000.

Oh yeah, I forgot to mention that the men sign a contract that I came up with. If they want to meet the day-of or within 24 hours, I take double what they’re offering. They never usually mind. They want a one night stand and if paying double gets them good pussy to keep them satisfied, they’ll pay it.

We eat some very expensive food and I have a couple more French 75s before he asks if it’s okay that we go to his place. It is also stated in the contract that we both agree on what will happen and if either of us feel uncomfortable, we can call it off. If I call it off, I don’t get all of the money. I put that in there to be fair, of course.

Tim takes me to his bachelor pad right near downtown. It’s a large condo a couple blocks from the bar scene, but far enough that traffic isn’t horrible. He looks nervous, like he hasn’t done this before. Maybe I should take the lead on this one.

I ask him to lead me to his bedroom and once we’re in, I slide off my shoes, bending over extra so he can see that there’s nothing under my dress covering my pussy.

“So, would you like me to suck your dick first? Or would you like me to bend over so you can have your way with me?”

I slowly walk over to him and start unbuttoning his shirt. I remove it from his arms. It’s always a relief when their bodies aren’t horrible. Next I slip his undershirt over his head. Once that’s on the floor, I trace my fingers down his chest and stomach, tracing the line of his pants.

“Can I have your dick sir?”

He unbuckles his belt as I’m kissing and nipping at his neck. I slide my hands down his front again, this time pushing his pants down. Then I push his underwear down.

I look down to some very disappointing news. His dick is very below average. Poor guy.

But I get to work. I get on my knees and let him fuck my face. He sits on the edge of the bed as I’m taking his dick deep and stroking his thighs with my nails. I hear him moaning and can feel his balls tightening up. He’s already going to cum?

I don’t even get to feel sorry for the guy before he’s moaning and cumming down my throat.

I stand up and kiss him on the lips. That’s always fun because some guys are so grossed out by it. He lays back on the bed, “Wow. That was the best head I’ve ever gotten. I’ll pay you extra just for swallowing my load.” Now that’s what I like to hear.

“Baby, I’ll take whatever you’ll give me.”

I try to hurry out of there. He calls me an Uber to get home because I didn’t want to sit in the car with him for 20 minutes… as bad as that sounds, it’s true.

I go home and brush my teeth, take another quick shower, and decide I’m going to show Ryan how I like to fuck.

Ryan comes over and I have the bed straps ready, candles lit, and the sex toys all cleaned and ready to go.

I tell him that tonight was fine, but I wanted to come home and have his dick. I immediately see the bulge in his pants.

“You like when I talk about how much I want your dick?”

“Fuck yes. You’re so sexy.”

“I have a surprise for you…” I grab his hand and lead him to my bedroom. His little gasp is cute. I’m not sure how much BDSM he’s tried or how kinky he is, but I’m going to rock his world.

“Are you tying me up? Because I don’t know about that…”

“Trust me, you’ll love it. You’ll be thinking about this night for weeks. Take your clothes off and lay down.”

He obeys. I tie his wrists and ankles. I slip a little blindfold over his eyes and kiss his neck and shoulders. I’m straddling him naked, with my wet pussy resting on his hard dick. I know this is torture for his already.

I lean down and lick his lips before kissing him. Our tongues are tangled and I’m already getting wet. I kiss down his neck, chest, swirling my tongue around his nipples, and continue down his stomach. I don’t touch his dick yet. Instead I run my hands up and down his legs, each time getting closer to his dick. I can see his body tense up every time I get close, and the disappointed breath he takes when I don’t grab it.

I lean down and slide my tongue from his balls up to the tip of his hard dick. “Oh fuuuck.”

“Feel good baby?”

“Yes, please keep going.”

I swirl my tongue around the tip, tasting the bit of pre cum that’s built up. He lets out another sigh as I let his dick fill my mouth and then my throat. I slowly come back up for air then take him back down my throat. I continue this slow deep throat for a couple minutes, listening to his moans and breaths.

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