My First Time Getting Paid for Sex.

The annoying, high pitch buzz went off again. I spent the night with my friend Brett and this alarm is not as rude of an awakening as rolling over and realizing I was naked with him. I use him as a booty call when I'm desperately horny and when I need free drinks and food.

I search for my bra as I try to avoid stubbing my toe on his furniture. I tip top around the mess we made and bent down to look under his bed. I notice a few condom wrappers, dust, and what looked like an accounting book. Still no bra.

I didn't want to wake him because awkward conversation would ensue and he'd be all cocky about how he "got" me again. I knew that I was already going to be late for my big meeting at work; my fault for sleeping through the alarm. I was racking my brain for an excuse I could make, but today was the big day I've been wait for to present in front of the board of directors at our publishing company. I needed to go home and take a proper shower, but I opted to use Brett's sink so I would give myself a chance at making it on time.

I don't have huge boobs, but being braless and having my nipples poke through the silk of last nights clothing distracted people from the wrinkles, or so I keep telling myself. I did my make up in the back of the uber that I couldn't afford, but I also couldn't afford to be late waiting for the subway or buses. I crunched on some breathe mints the uber driver had and combed my hair with my fingers as I thought about how I really needed to stop drinking and staying out on weeknights. I really need to get my life together at some point.

I hate living in outside of Manhattan because it was so difficult to get into the city during rush hour. I need to make friends with or start sleeping with guys that lived downtown rather than Brett's studio.

I'm braless, smelling like semen, probably wearing a bruise somewhere from sex with Brett last night in addition to the same clothes from yesterday. My co-worker immediately notices and I give her the "don't start" look. I'm self conscious that my panties would show or that my scent of day old + sex panties would waft around the office. I could feel eyes on me as I walked by and I was too self-conscious about my nipples to have a conversation with anyone. I ran to the first aid kit to try and find band-aids to put over my nipples, but the box was empty. Who in the hell would put the empty box back in the wall mounted kit if it was empty. Well I followed right along because I didn't know who to notify and honestly I didn't care. I put the box back, clipped the clips closed and ran to my desk.

I grabbed my laptop and walked to the meeting. I took a few deep breaths, tried to strike a power pose, and waited for the room to quite down. I go to bluetooth into the projector and realized that my computer is at 6% battery. Great! I'll just wing this. I crush the presentation without a projector and slides. I'm feeling really accomplished. I had a good day at work yesterday, celebrated with drinks (for free), had a guy friend go down on me, and crushed my presentation today all while being under prepared and braless. I'm just that good!

The feeling that I was able to pull the wool over everyones eyes and just use my talent to wing it is amazing. Well anyway, hopefully I'll get that promotion soon that I've been passed up for in the last two cycles. I could really use the money. I needed to catch up on bills, and I wanted a break from dating guys just for the food. For once I just want to not put in any effort online with dating apps just to pretend to be interested in some random guys frisbee club so I could eat something more than a $12 salad. I was literally meeting different guys for coffee, lunch, and dinner just to make it in NYC.

I sped off to my second job bartending immediately after I finished work. I wanted to go home and change, but it's across the bridge and I wouldn't make it in time. I usually pack a bag, but you know how my morning went. I worked up a sweat walking there and I could tell my deodorant is not doing what it advertised it would do. I had this clean musk about me and I was sweating a little. Not a great look.

I say my hellos, clock in with my manager, and then bee-line to the bathroom. Again I use the sink to freshen up. I found a sleeve of napkins that I used to fan and air dry myself and wipe up what mess I could. I felt better, but was still a little self conscious.

I start my shift and flirt a little extra hard trying to earn extra tips. I kept saying to myself that the nipple no bra thing is a good thing... nips for tips, nips for tips, nips for tips... I kept repeating to myself in my head. I notice Phil, a regular that I don't know much about other than he's mid 40'sish, a little grey, dad bod, but handsome and really well put together. He always comes in dressed business casual, has a deep voice, and a fatherly sense about him.

"Hey, Phil! The usual?" I asked trying to make eye contact. He never looks at me in the eye. He's always reading or on his phone. His large hands make his phone look small. I've always noticed his hands and forearms. They were veiny, well defined, humongous, and hairy. I know it sounds weird, but on him, hairy hands just seemed so... I don't know... masculine.

I've definitely thought about him while toying with my vibrator at home. I figured he'd be really good and strong fingering me. I've visualized his big hands on my small, slender figure, but today he did make eye contact. I flirt with him every chance I get, but he's always been so mysterious. I didn't care since he was a really good tipper.

I purposefully bent down to let him see down my shirt. I bent over to reach the "ice" or whatever right in front of him. I shimmy my hips and wiggle my waist to get my shirt to come up a little and show my toned tummy off as I reached for whatever when I'm right in front of him. He usually doesn't even respond, but today he definitely did. His eyes were glued to me. I made sure to smile and wink a few times. Not enough to be creepy, but definitely send the message that I liked him for more than just his money.

"Careful, you're going to break a lot of hearts like this." He said as he looked me up and down.

I approached him while hugging a tray in front of my chest just to set it aside on my hip when I got closer. Almost as if I was revealing my chest to him.

"That's the point, Phil! The more they're heart broken, the more they drink." I coyly responded.

We traded a few more light jabs before I went for the kill. "You know, I see you hear all the time, but this is the first time we've ever really talked. You shy or just don't like me?"

"I figured you have enough guys to talk to, I don't want to add to the list. Besides, if it were up to me, you're not the type of girl I would spend much time talking to."

"Hey! I know we're not in the same league, but you don't have to be so hurtful." I quickly retorted with just enough attitude to show I'm a little offended.

"Oh, I didn't mean it that way. I'm sorry! And now that I'm explaining it, I feel even creepier." Phil said earnestly.

"Oh you're not creepy at all, Phil. It's if I don't like you is when you're creepy."

"Well thanks, a bartender that likes me. I must be an alcoholic then."

"No, just a good tipper!" I don't know why I said that, but I was really pushing this money thing tonight.

"Well you're my favorite bartender, but it's not because of your stiff drinks."

I couldn't tell if he was flirting back until he winked.

Phil leaned in towards the bar. He beckoned me closer and when I did come closer he rest his hand on my upper arm and leaned in. "I'm in room 921 across the street. What time are you off?"

"In an hour." I said flatly staring at him.

I'm not sure why, but I figured this was my chance to finally get to know him. I was nervous since I hadn't properly freshen up and because he's so intimidating. He's successful, good looking, and could probably get any woman he wants. What's he want with lowly bartender like me?

The rest of my shift dragged by. I was mixing up orders and mistaking drinks. I couldn't think straight. I downed a couple of shots using my tips to gain a little liquid courage then walked across the street. Phil was waiting for me in the downstairs area, thank god! I didn't want to play this desperate pretty woman scene out in my head where I had to ask the front desk to ring up room 921.

After some small talk, mostly me talking nervously and him looking annoyed that I was talking too much. He grabbed my hand and led me to the elevator. He pushed the buttons then turned to me and placed his greek god of a hand on my waist. His fingers ran all the way up to my abs, wrapped around my back, and even slightly flirted with my under/side boob.

I walked forward expecting him to pull me in for a kiss or a hug, but he pushed me back against the wall with force. I think it seemed forceful because I was trying move toward him at the same time. I had to admit, feeling his strength was a turn on and knowing that he was taking control made me wet. I didn't anticipate sex, but at this point, I would have given him whatever he wanted.

His other hand slid up my thigh and towards my crotch area. I could feel the warmth shooting throughout my body and it was making me self conscious again. I started to talk, but he just placed his index finger over my lips to shush me. It worked. I started to open my mouth a little to inquire what was going on but just left my lips parted.

He brushed my lips with his thumb then made his way into my mouth where I instinctively started to suck it. We held eye contact the whole time and it was so hot. For a moment I couldn't gather myself so I leaned my head back and closed my eyes pressing my hips, waist, and pussy into him trying to feel his thigh or hand or something.

He pulled me from the elevator and sent me to get ice down the hall. He specifically said just a few cubes and to hold it in my hand. When I came back, I felt like a cheap whore knocking on the door - I bet he planned this. He opened the door completely naked and pulled me inside. His confidence was fun since I rarely see it from anyone. The shower was going on full blast and I could tell he put it all the way to hot because steam was escaping the bathroom. He took the ice and slide it along my neck. He then put it in his mouth and used it to kiss me as he undressed me. It was scintillating. I had goosebumps all over and it wasn't just from the ice.

He neatly folded my clothes as I stood there completely naked and then placed them in the safe. He locked it. I thought this was so weird. I felt trapped all the sudden. What if I wanted to leave? I needed his permission or I'd have to leave naked?

"This is, I assure you, part of the plan. I want you to feel submissive to me. I want you to need my permission. I control you." He said in his deep voice, but this time instead of a fatherly vibe, it was more of a boss kind of vibe.

"What do you want me to do now? You can have anything you want. I've been waiting for this. Like, seriously, I've always wanted to fuck you." I blurted out; not knowing how to proceed. If I should wait for his instructions or try to take action. It was all very new and all very exciting.

He pushed me into the bathroom where I sat on the counter while he used the fast melting ice on my thighs and over my clit and lips. It was so a new sensation. It is almost painful, because it is sensitive, but I loved it. The steam made it hard to see, even just him a few inches in front of me. I loved it. It was fun, mysterious, new, and really hot with the overload of senses. I was essentially blind getting fucked by an ice cube in a hotel room with a man I barely knew.

I stopped him and asked: "Wait, you don't want to take me back to your place?" Half curious why he didn't and half offended like I wasn't good enough again.

"I'm from Seattle. I'm just here on business. I work here a couple times a month and I stop in to see you move behind the bar."

"Oh, you're there so often, I thought you were local, but I guess regular doesn't mean local..." I started to think out loud.

Then he put his big hand on my pussy and slide a couple fingers in. That sure made me stop talking and take a huge audible deep breath.

As I was trying to catch my breath I asked: "How many fingers is that?"

"Just two." He replied deeply in my ear letting his lips caress them and the side of my face.

I forgot how big his hands were. He fingered me until I came right there on the counter in the make shift steam room. He pulled me closer to the edge and spread my lips apart. He positioned what I imagine is his dick right there and just fucked me. I felt like a whore. It was sudden and unceremonious. He didn't say anything just fucked me.

His veins felt like ridges and his head was huge. As he pushed deeper, his shaft was girth-y and his rhythm was unpredictable. I guess most middle age white guys with big dicks just fuck like this. He doesn't care about my pleasure, he just wants to nut. I felt like an even sluttier whore. The worst part is I'm actually enjoying myself. I love being treated like this, getting fucked roughly, and the guy isn't emotionally interested in me. It's like I have to try harder to impress him. So I squeezed my pussy walls as tight as I possibly could and really tried to be tight for him.

It wasn't long before he pulled out and jizzed on my stomach. Again, unceremoniously.

I was sweating and horny, trying to catch my breath. Phil picked me up with my legs wrapped around him and walked towards the bed. I wanted more of his man meat. I loved getting his big dick and I loved how the texture of his veins was so amazing against me. I looked down, being able to see for the first time without steam, at my pussy. It was raw, red, stretched out. My lips looked destroyed. He choked out my cunt and buried it.

His dick, still dangling ever so largely between his legs like an alien member was covered in a milky substance. It clearly was glistening with pride like he just made me crave him, and knew that it pleased me beyond what I can do to myself. As I looked up from his massive dick I noticed he had his phone in his hand again. I couldn't stop looking at his monster dick, but I did notice the light of his camera was on. He typed a little on his screen then set it down.

"I just took a video of you naked standing in front of me and cock wet from your juices. Don't worry your stomach looks flat and shiny with my cum on it." He winked.

Before I could react, Phil moved towards the safe, took out my clothes and ordered me to put them on. He took pictures of my getting dressed, bending over to pull my panties on, etc. I was really uncomfortable, but I was scared and didn't know how to stop him or what to say.

Again being wise and social perceptive as he is, he said: "Don't worry I won't show anyone. This is for me. It's for my safety. It's blackmail. I don't want my job or wife and kids to know. If word of this ever even thinks of getting out I'll have a little something to motivate you to keep your lips closed. Unless you want to open those pretty little lips up again for me?"

He was so nice, now he's a jerk. A jerk for taking photos and video of me without my consent. A jerk for fucking me like a whore. A jerk for talking to me like this. I won't admit this, but I loved it. I loved how cocky he was. I loved getting talked down to and him telling me what to do. I loved how in control he is and how helpless I am. I loved that he talked shit to rather than respectfully ask if it's okay to touch my vagina or pull my panties down or touch me. I'm conflicted, since I want to be taken seriously, but I really enjoyed getting this treatment.

He reached into his wallet and handed me a few hundred dollars. "I'll come see you again in a couple weeks." He said as he guided me towards the door.

What!? What. in. the. actual. hell?! I didn't know what to say. I'm stunned and just stood there. I left because I didn't want to be seen like a lonely loser desperately seeking attention standing in front of his door reeking of sex and semen.

The whole commute home I was conflicted. Should I feel cheap for it only being a couple hundred dollars? Well maybe that's a lot for other women. It's clearly a lot for me. I wanted to return it and slip it back under his door, but I could really use it. I would have fucked him for free, did he do this out of pity? Does he think I'm a sugar baby or something? I guess I could get used to being a sugar baby, but I don't want to, but it's great.

I felt empowered and sexy and fulfilled and unsatisfied and cheap and used all at the same time. I would love if I made a few extra hundred bucks every time he was in time, but does that make me a hooker? Will he ever pay me again? I've wanted to fuck him for so long that I wanted it to be amazing like he actually liked me and desired me. Now I'm just some business bimbo. A place for him to dump his cum. What will actually happen with the photos and video he took?

I was scared. But I also couldn't get over the fact that a guy like that would want to fuck me. That he got hard for me. That he came because of me. It was like an honor that he chose me. I was still scared, but I was also horny... still. He felt so good and he did things no other smaller guys (like Brett) could. He is a man. He is my man? Wait, no, too far. He barely knows me and I don't even know him.

A few weeks went by. I ferociously used my vibrator until I was raw, thinking of Phil every day a couple times a day for all these weeks. I was serving drinks again and I heard a deep voice behind me say playfully: "You still working for tips?"

I smiled as I turned around and told him quietly: "If it's yours, and only if it's not just the tip."

He didn't even order a drink he just got up and left a room key on the bar for me. I quickly snatched it up before other patrons could see it. The confidence of this guy! Literally, like, right there in front of everyone. For all the people to see. He leaned in and said that he'll have a bottle of champagne waiting for us in a bucket full of ice this time. I blushed as he walked away. In a few hours, I think I'd be more than blushing.