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First time for everything

The things you do in college
Let me start off by saying that I have fantasized about alot of things (and tried a number of them); group sex, sex with trans guys, anal, bondage, and the list goes on. I love sex, and I like to get a little adventurous. One thing I never thought I would try would be taking money for sex. It’s not that it offends me, or that I think women demean themselves by doing it. I guess I just never really pictured myself doing it until, well… I found myself on my knees in a very expensive hotel room.

The story really begins with me getting a new job at a posh hotel with a really, really nice restaurant attached to it. It was the kind of place that sees a lot of business conventions with guys from big corporations. Even though we hated the long hours, the tips were great which helped a lot with paying for school. I think almost everyone has that story about how broke they were in college, but at that particular time my bank account particularly low. At this point it is important to realize that when I say low, I mean it had an awful lot in common with the Titanic. I had had some unexpected lab expenses and I still owed 700 to the mechanic for fixing my car.

Most of the waitresses were college students such as myself, and we were pretty used to flirting with the guys at these conventions to pad our tips a little bit. Maybe I had been doing it a little shamelessly out of desperation but I didn’t think I was giving off the kind of signals I apparently was. The whole time I had been really flirting with this table of guys in suits and smiling and laughing at all their come-on’s. Finally, the end of the dinner comes, they pay with a card, and when I make my second trip to the register to enter in the total I just stop. I freeze as I look at the receipt with the signature. The tip was 250. I had never gotten a tip like that and I was just about to jump with joy when I noticed the little note underneath the receipt. It said “If you are interested in a better tip come to room 1421 after your shift.” Another waitress came up behind me and needed the register so I pocketed the note and finished entering everything.

It wasn’t a lot of money to guys like that, but it was a lot to me. It got me thinking for the next few hours until the restaurant closed at 11. It was so strange, I went through these different emotions. At first I was a little insulted, and then I was kind of flattered, and then I decided not to do it just out of angry resentment. However, the more I thought about it, I kept going back to how much it would help. The restaurant closed and I was finally able to get out of there about 11:30. I was about to grab my jacket and leave when I remembered the note in my pocket. I thought that if I do this this one time, I could fix so many problems and before I knew it I found myself in the bathroom, combing my hair out really quick and putting on a little bit of lip stick and touching up my makeup.

Now, I honestly don’t think I am anything special, or really that unique when it comes to looks. I am just under 5’6” with brown hair and brown eyes. I have a decent figure, nice round hips with a flat tummy and depending on how it fits I am either a large C or a small D cup. When I was looking in that mirror I kept bouncing back and forth between being kind of disgusted with what I was about to do, like it made me less attractive; and thinking that it is my body, I am proud of how I work on it and if I can use it to succeed I should. I wavered for a little bit and then headed to the elevator.

That was one of the longest elevator rides of my life and an even longer walk down the hallway. There are security cameras but I know they never check the footage unless there is a problem. I just hoped that none of my co-workers saw me and asked what I was doing. I finally arrived at the door to room 1421. There was a renewed wave of hesitation where I almost walked away but I finally knocked on the door. I honestly had missed who the card had belonged to so I wasn’t sure who I was going to see when it opened.

Finally, the door swung open and I saw who he was. He was only a couple inches taller than me, shorter than I prefer guys, early 50’s, overeight but with bright blue eyes and a smiling face. I didn’t recall his name immediately but his flirting had bounced back and forth between lewd and articulate. He gave me one of his bright, wide smiles.

“Hello,” he said in a tone dripping with the same kind of excitement eight year old boys have when they are opening big presents wrapped in bright colored paper,” I was almost sure you weren’t coming. He stepped aside and with a wide gesture he ushered me into the room.

“I almost didn’t,” I replied in a voice that I hoped didn’t sound as nervous as I felt, and I walked into the room. I looked at the big suite, the view of the city out the large glass windows, very spacious. I realized what I had said and I turned around to look at him, my cheeks getting red.

“ I mean, I… usually don’t do this kind of thing. My first time, so to speak” I said sheepishly. I set my purse down on the table and look at him as he finished closing the door and casually strode to the bed, sitting down. He looked up at me and I could see his eyes, wide and staring, drinking me in. I blushed some more and looked down a bit. He really did seem excited, like a boy about to open a present.

“N, Neither do I,” He stammered a little bit, “But I just, I just needed to do something. I’m not gonna tell you my life story but it has been kind of all work and no play for the last few years, no social life outside of these stupid conventions. You are just so beautiful, and you seemed so happy and flirty. I need that, and I am willing to pay.” As he went on, he got less bashful, his confidence was that of a business man closing a deal. Honestly, that impressed me; plus I was more than a little flattered by his compliments. I paused to think a moment. Apparently he was a better businessman than I thought, his next few lines came out almost like he read my mind.

“Before you decide, let me say this. I don’t want to hurt you, I want a willing, hungry woman that I can enjoy for a night.” Now that this was more like a business pitch I felt him taking control, which is something that is a turn on for me. He picked up his wallet and pulled out a big stack of green. “I can assure you I am clean and healthy; well at least no STD’s and I even have the test results here,” He paused to pull out a stack of papers from the drawer and set them on the nightstand. “I have another 250 if you want to continue, I have an optional clause if you are interested”.

I swallowed hard, I was pretty much sold but his mention about a final point made me more than a little nervous. “Me too, about the STD thing that is. Um… what kind of clause do you have in mind,” I said meekly. His excitement was palpable, almost something physical as he took a breath while trying to keep his composure.

“I always do the safe thing, and I even have condoms, but if you let me take you bareback," he paused trying to contain his anticipation as he set down the rest of the stack of cash, "there is another 1,000 in it for you. Interested?”

My jaw actually dropped from amazement. He stared up at me in hope and anticipation. I could feel his eyes roaming up and down my body as he waited. A few moments went by as I debated back and forth. He did have the cash on hand, and he did have the doctors report right there. I desperately needed the money and the amount he quoted would not only pay for the car and the lab fees but put me ahead for the month. I opened and closed my mouth a couple times, almost saying no to the option but thinking I am on birth control, my ex and I had done it bareback and I had never had an issue that whole time. Finally I looked up at him and smiled.

“I agree to the option,” I tried to use a fiery, confident voice and judging from his reaction (He actually almost clapped for joy) it was more or less on the mark. I took off the black vest that we wore as part of our uniform and tossed it away. As I was about to undo my bow tie he stood up and motioned for me to stop.

“I want to unwrap my present.” He looked at me with so much hunger and anticipation that I got nervous for a second. As he walked towards me I wondered if I had made a mistake. He looked me in the eyes and then started to loosen my bow-tie. His hands were deft from lots of experience at dressing for work. I tried to strike a pose as he went but wasn’t really sure how to stand. He unbuttoned my dress shirt and un-tucked it from my skirt. The was surprisingly careful to not grope me as he undid the shirt. Then he stepped behind me. Unsure what was happening I looked down, trying to look demure I guess? I don’t know, I have never been a hooker before.

He turned me to face the mirror and then pulled my top away like he was revealing something on a stage. As he looked into the mirror at the two of us, his hands came around and groped my breasts. He obviously never worked out but his hands were surprisingly strong as he groped and kneaded my tits. I actually started to get wet and felt my nipples harden. As stood there, listening to him breathe and mutter about how beautiful I was, it suddenly dawned on me that this guy was shelling out 1,500 to have sex with me. That was kind of a trip and it made me feel like I really needed to make it worth it; after all, I always liked to say I have a good work ethic.

I snapped back as I felt him lift up my dress and slide a hand underneath to my crotch. I let out a soft moan as his fingers rubbed my clit through my panties.

“I’m glad you seem to be enjoying this as well,’ he spoke softly, almost breathlessly as he fingered my pussy. He was right, lack of personal life or not he knew enough to make me wet and I let a shiver of enjoyment run up my body. I did my best to purr in a sexy manner, not necessarily because he was doing that well, but because I thought it would turn him on.

I leaned back against him, pressing my ass against his crotch as he fingered me. I couldn’t believe it, but I was really starting to enjoy this. He stopped for a moment and fumbled with my skirt, then getting it to unzip, he let it fall to the ground. He ran his hands up and down my body and then walked back to the bed, sitting down. He stared up at me.

“Take off your bra and panties, slowly, but leave your heels on.” He was rubbing his crotch. I could see he was rock hard but couldn’t quite get an idea of what he had in store for me. I smiled at him and slowly complied with his command.

“Like this?” I asked in what was hopefully a saucy, sexy voice. He muttered various affirmations as he continued to rub his hard cock through his slacks. I had never tried performing but I was really enjoying his undivided attention. Unclasping my bra and letting it fall away to show off my breasts, I rubbed them, playing with them for a moment, and then lifting them to my mouth and licking my hard nipples. Then I reached down and slid off my panties. I stepped out of them and walked closer to the bed. I put one of my heeled feet up on the edge of the bed and reached down to run a finger across my pussy. I moaned a little louder for him as I did it.

“Oh my God” he said as he reached up and massaged my thigh with his free hand. He rubbed it up and down while I played with my pussy and then finally reached forward, fingering me again. I moved my hands away and played with my tits, doing my best to be sexy. He slipped two fingers into my pussy and thrust them in and out slowly. I gasped loudly and looked down at him, my cheeks red and flushed. My pussy was dripping wet at this point.

I actually hadn’t been this turned on in a while, I couldn’t believe it. He was older, chubby and definitely not the type of guy I usually went for but he wanted me so desperately and was happier and more appreciative to get me than any guy I had been with in a while. I reached down and took his hand. As he drew his fingers from my pussy I moaned again. I lifted his hand up to my mouth and slid his fingers in between my lips, sucking on them. Licking my juices off them. I was enjoying the hell out of this.

“Would you… would you suck my cock please?” He was panting heavily, excited and turned on.

I guided his hand from my mouth to my left breast and pressed it hard against my chest. I let out a loan moan and then looked him directly in the eye and said with a smile, “sure thing sexy.” I slowly went down onto my knees. I pushed his legs apart and pushed on his chest so that he laid back on the bed. I let my hand trail down over his chubby belly until my hand rested on the bulge in his pants. I gripped it and gave it a few squeezes while he moaned. Then I unzipped him and pulled down his expensive slacks and his boxers.

I was pleasantly surprised by what I found. He wasn’t any longer than average but he was as thick as a coke can with a flared mushroom head. “Oh my god, you have such a sexy cock."

I was being completely earnest. I leaned in and ran my tongue up and down his shaft a couple times, making sure to moan while I did it. I gave it a few light kisses. He groaned as I did this and his hips thrusted into the air involuntarily as my red lips brushed against his cock. I put my lips against the tip of his cock and tried to take it into my mouth. He groaned and gripped the bed sheets but I couldn’t get it very far. I tried a few times while holding his balls in my hand and playing with them gently.

“You’re just too big,” I said using the best sexy voice I could muster. He sat up, he was panting from excitement, “Is there something else I can do for you?” I ran my hands up his belly and his chest, cupping his face. I couldn’t believe how much fun I was having doing this for him.

He patted the bed next to him, and stood up. “Sit here please.” He may have phrased it as a request but it carried the same authority that I imagine he reserved for the board room. He stood in front of me, his thick cock almost to my face as he brought his hands up, and gingerly touched my face. I closed my eyes and nuzzled my cheek into his hand, unsure what else to do. We stayed like that for a few seconds and then let his hand drift down to my chest. Now he gave me a rough shove, pushing me onto my back, legs in the air. I squealed and gave a shout of delight. Part of it was for him, but part of it was very real. He ran his hands down my body, squeezing my breasts, feeling my tummy, grabbing at my hips, exploring my thighs . He was admiring his purchase, taking time to savor what was to come.

I looked up at him and licked my lips, spreading my legs. I reached one hand down and rubbed my dripping wet pussy. He gulped and cleared his throat as he moved in between my legs, one hand grasping that fat cock, the other grasping my hip. The tip of his cock brushed against my pussy and an electric sensation pulsed up my spine.

“You are the most beautiful woman I have ever had.” It was a quiet statement, almost too soft to hear and I was about to react to it when he suddenly, and roughly thrust his coke can cock into my pussy. He pushed balls deep right away, forcing it all the way in.

I arched my back and shouted “Fucking shit!” Which was an entirely real reaction. I pulled at the bed sheets and bit my lip, cursing. He was gripping my hips, hard. He wasn’t trying to hurt me but he surprised me with the strength of his grip. I could tell it would leave a bruise but as he began to draw out I took a deep breath, closing my eyes. Just before the tip was about to slide out, he thrust back in hard and I actually screamed this time. Now I was panting as my heart hammered away in my chest, my breasts rising and falling. He paused, suppressing a little shudder and I thought he was going to cum but then he started pounding away at my pussy, fucking me hard.

“Play with your tits while I fuck you” he commanded and I was more than eager to comply. He thrusted into me over and over while I squeezed my tits, pulling on my nipples, rubbing them while he watched. This red faced man more than twice my age fucking me, and I was loving it. His big fat cock was stretching me, making it hurt and his balls were slapping against me as he fucked my pussy.

“Fuck yes, cum in my pussy!” I can’t believe I just said that shit out loud to a stranger, but there it was.
 
He was ramming his cock into my pussy over and over again when he just stopped and pulled out, I took a long shuddering breath. I was panting almost as hard as he was. He grabbed me and rolled me onto my belly, pulling me back to him so that my legs were hanging over the edge of the bed. He once more guided his cock to my pussy so that the tip was just parting my labia, then placed one hand firmly on my back, pressing me into the bed, the other grabbing my hip. He loomed over me, his bulk pressing me down. He rammed his cock into me hard and immediately began thrusting away. Grunting, straining and pushing against me. He rutted like an animal as he used my pussy, and I didn’t even have to pretend to enjoy it.

He moved the hand on my back down to my hips and gripped hard again, hurting me a little but I didn’t care. He was using his stubby fat cock to stretch my pussy and I moaned loudly with each thrust. After a few moments of his rutting his pace began to slow. He thrusts were harder, deeper, forcing himself into me and I screamed through clenched teeth. He thrust one final time, pushing me into the mattress so hard that it forced the air out of my lungs. I gasp and breathe deeply as I felt the sensation of this thick cock pumping his cum deep into my pussy. He groaned and rested on top of me as we both panted, recovering from the moment. He rolled off me and I rolled onto my side to face him.

A few moments of quiet talk and he finally dozed off. I slowly dressed and took my money, but before I left, I found his phone and entered my number. He never had to pay me for sex again, but when he does call me he likes to spoil me. That however is a whole different story.
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