Working Girl Pt. 01

My name is Emily. I've just graduated college with a nursing degree at twenty-two years of age. I truly thought I was going to have to drop out after my second year. This is the story of how I got through those last two years.

It started at the end of my second year with a call at 2:00am from my mom. She told me that Dad had had a heart attack. He was alive, but in bad shape. After the semester ended, Mom said she had good news and bad news. The good news was that Dad was going to recover. She broke the bad news to me. Their savings were being drained by Dad's treatment. They would not be able to afford to keep paying for my school. I understood the situation but hoped I could make the money on my own and also would try to get need based scholarships.

I had already secured a summer job at a resort hotel working as a waitress and maid. I quickly applied for several scholarships and grants with the hopes of keeping me at my school.

The money I made from the resort was okay but nowhere near what I would need to stay in school. I made friends with the head hostess. Her name was Lisa; she was in her mid-thirties. She suggested that I flirt more to get better tips. Many of the guests were there on business and liked to flirt with the girls. She was right, especially the middle-aged guys. I'm petite, 5' 1" with natural red hair. I had just turned twenty-one but most thought I looked sixteen.

The bad news about the scholarships and grants came all at once. I had been denied without explanation. Lisa happened by my room after I received the news. I tried to hide that I had been crying but broke down when she had me tell her what was wrong. She comforted me for a while and then told me not to work my shift that night. I cried most of the night. I didn't call my parents deciding that they had their own troubles.

The next morning Lisa showed up at my room. We talked for a while about my troubles and how to solve them. Lisa then looked at me strangely, "How badly do you need the money?"

I wiped the tears from my eyes. "I would do anything. Work triple shifts. Whatever it takes to make the money."

"I might have a way for you to make the money you need. You may not be willing to do it," Lisa said looking at me cautiously.

"Lisa, I will do anything - scrub toilets, carry the trash, whatever."

"It's not that. Remember when I told you to flirt more and you would make better tips." I nodded. "What I'm suggesting is along those same lines but a little more. You cannot breathe a word of what I'm about to tell you to anyone. You got that?" Again, I nodded. "Many of the guests are business men who will pay for some flirting and some extras. Do you get my drift?"

"Are you suggesting that I be a hooker?" I said in disbelief.

"Honey, I'm suggesting you use what God gave you to get you the money you need. I'm not talking about walking the street. It was easy for you to flash that smile and bend over at the appropriate time to get those men to give you an extra twenty. I'm just suggesting you play on their fantasy for the money you deserve. You're not a virgin, are you?"

"No, I've had two boyfriends that I've done it with. But this is different; I don't think I could do what you're talking about."

"The offer is there, you think it over. I will see you at your shift later this afternoon." Lisa said hugging me.

After Lisa left, I got to thinking about all that she said. My initial reaction was, 'Hell no, I can't do it.' But she was right. I would talk in my sweet little girl voice and bend over to let the middle-aged guys see my cleavage. I knew what I was doing; I was giving them a taste for money. My common sense was being overridden by my desperation. I kept looking at my rejection letters, getting madder and more desperate. I didn't know what to do but Lisa's way was looking more and more like my only way.

During my shift, I was extra flirty. I unbuttoned an extra button on my uniform blouse and was very touchy. The guys responded with bigger tips. On my break, I counted the money. I was doing good, but it was still a drop of what I needed.

Lisa walked in seeing me counting my money. "You're doing good today."

There was an awkward silence in the room till I spoke up, "Okay, how would it work?"

Lisa took a deep breath looking around to see that no one was around. "If you're sure, I will give you a room number and you will take a tray to that room, and announce room service. They will have already paid their service fee of $150 to me. What you charge is up to you. I would suggest $500 for an hour and more for longer. What you do is up to you. If you have problems, you just call me. But these are business men who don't want any attention on what they are doing. I have a supply of condoms that are a must. With your cute little girl looks, you can make a killing."

"Alright, I will try this. When do you want to start?" I asked with a little tremble in my voice.

"No time like the present, I have a nice guy who will be perfect for your first time. Your shift ends at 9:00 so about 8:45 get cleaned up and see me right when you clock out. I will give you an order to take to his room. I'm going to tell him this is your first time, so he will understand if you're a little nervous."

"Oh shit, I don't know if I can this, Lisa. That's too fast."

Lisa looked at me sternly. "If you want to back out, now is the time. After I make the call, we are not going back."

I thought of my situation and decided I had no choice. "No no, I can do this, I'm just nervous. What should I wear?"

"If you have some lacy bras and panties, go put them on at your next break. Once you leave stop off and put on some red lipstick. With your red hair and complexion, you will be irresistible."

On my 7:00 break I went to my room. Fishing through my stuff, I found a black pantie and bra set. I put the bra and pantie set on, looking at myself in mirror. I thought I looked pretty sexy. I found some white stockings that reached just above my knee. I decided I would put those on when I put my lipstick on.

My nerves set in as the clock inched closer to nine. About 8:45, Lisa taped me on the shoulder. "Are you ready?"

I gulped, "I think so. Let me go wash up first."

When I came out, Lisa made a production of sending me off to a room service call. I thought it was a little excessive, but I now understood the other times it happened right at shift end with the other girls. She gave me the tray and the room number. It was Bob in room 212. Lisa said that she had already negotiated $600 for an hour for me. Bob had been told that it was my first time so he was paying extra above the normal rate.

Lisa handed me a fruit plate and the bill. The more legit, the less suspicion. "Use the bathroom on the second floor to put your lipstick on. Just relax, it will all be fine."

I would normally take the stairs to just the second floor, but my legs were too wobbly. The elevator was better anyway as the bathroom was just as you got off. I slipped into the bathroom to put on my lipstick and stockings. I knew was past the point of no return, so I just tried to calm my nerves.

I tentatively knocked on the door of room 212, announcing, "Room service."

A casually dressed man that appeared in his late 30's or early 40's appeared at the door. I quickly noticed the wedding ring on his finger as he let me in the room.

"Emily?" He asked.

I gulped again putting the tray on the table as he locked the door behind me. "Yes, Lisa sent me."

Bob looked up and down, checking me out. "Oh my God. Lisa said you were cute, but you're amazing. I'm sorry. That was rude, but you are gorgeous. You waited on a group of us at the restaurant and we all talked about how hot you were."

Blushing, I said, "I remember you, you all gave me a big tip. Thank you."

"Let's get the formalities out of the way. Let me have the room service ticket. I will sign it and give you a nice formal tip that my business will pay for." Bob then counted out six one hundred-dollar bills laying them on the tray.

I just stood there, looking lost. I finally spoke up, "I'm sorry, I'm just a little nervous not sure what to do next."

"It's okay Emily, let me walk you through this. Are you comfortable giving me a hug?"

I nodded and opened my arms to Bob. For the first time, I noticed that Bob was a good-looking man. Bob took me in his arms for a gentle embrace. I melted in his arms. As Bob released me, I reached up, kissing him on the cheek before backing away.

"Can you take off your blouse and skirt to show me what you have on underneath?"

I tried to do a sexy strip, but it felt awkward as I unbuttoned my blouse and slid my skirt to the floor. I felt strange standing in front of this stranger in a lacy bra and panties, but I felt sexy, the way Bob was looking at me. "Wow, you look incredible. How about another hug?"

Again, I held my arms out inviting Bob in. This was tighter, and I felt his crotch rub me. It was obvious his cock was hard as he rubbed his crotch against me. I leaned up, this time putting my lips on his. Bob pulled back in surprise.

"I'm sorry, am I not supposed to do that?" I asked feeling that I did something wrong.

"No, I wasn't expecting you to want to kiss. I would love to have you kiss me."

We resumed our embrace with our lips meeting. I had always liked kissing and Bob was a good kisser. Our tongues played as we held each other tight. Bob's hands began to roam over my body, landing on my tits over the silky bra. I reached behind me to release my bra to give Bob access to my breasts. Bob fondled my tits and leaned down to suck them.

Bob picked me up and laid me on the bed. He kissed me again passionately. I whispered in his ear, "Do you want to take my panties off or do you want me to?"

"Mmm, I would love to. I'm dying to see if that beautiful red hair is natural. I'm betting it is." Bob got between my legs, pulling my panties down. "Mmm, I was right. That is a beautiful muff. Don't let anyone talk you into shaving it." Bob kissed my pussy then shoved his tongue inside me. "You are so juicy, you taste great."

Bob continued to kiss and lick my pussy. I actually forgot I was getting paid to have my pussy eaten.

I was moaning loudly as an orgasm was building inside me. "Oh Bob, that feels great. I'm about to cum."

His tongue went faster, and he inserted a finger inside me finding my clit. My body started to shake as my legs contracted around Bob's head.

"Fuck yes," I called out.

I lay back on the bed while Bob crawled up next to me. "Bob, I thought I was supposed to make you feel good?"

"Oh sweetie, tasting you and feeling you cum was incredible."

"We both know this is my first time but isn't there something wrong with you being fully clothed while I have only my stocking on. I think I need to take your pants off, so I can suck your dick."

Bob stood up next to the bed pulling his shirt off, "Oh please, can you do me a favor before you do?"

"Sure, whatever you want."

"Re-apply your lipstick before you start. You have the most luscious lips. I want to see those bright red lips wrapped around my cock."

I quickly went to my purse, fishing out my lipstick. After coating my lips, I sat back on the bed, unsnapping his pants. His boxers quickly joined his pants on the floor. I made kiss marks on his dick in several places before taking him into my mouth.

Bob moaned loudly as I worked his cock in my mouth. "Oh baby, you are incredible. Your lips look as good as they feel on my cock."

I sucked hard and stroked him. I could sense that he was getting close to cumming.

"Emily, I would love to cum in your mouth if you will let me."

I looked up at Bob and just kept on sucking.

"Get ready, here it comes," Bob grunted before filling my mouth. I struggled to keep it all in my mouth and choked a little before swallowing his jizz.

Bob climbed on the bed with me, hugging me. "That was incredible. Thank you Emily. Oh shit, would you look at the time?"

We both looked at the clock next to the bed that read 10:15.

"My hour is up."

I leaned over and kissed Bob on the lips. "I can leave if you want but I will feel weird leaving my first time without fucking."

"You are something special; I'm dying to fuck you. It will take me some time to get hard again if you have the time," Bob said, kissing me back.

"I have time. We could spend the time kissing if that would help?"

Bob wrapped his arms around me, pushing his tongue into my mouth. Bob rolled on top me after some heavy making out. Bob overestimated the time it would take for him to get hard again. Bob continued to kiss me while rubbing his not hard cock against my pussy. We were both enjoying the rubbing till I felt the unmistakable sensation of his dick slipping past my pussy lips. I let him pump me a couple of times before I stopped him.

"Bob, Bob." He finally stopped fucking me and opened his eyes. "Condom Bob."

"Oh shit, I'm sorry. It feels so good." Bob continued to slowly fuck me.

I knew I should have stopped him, but it did feel good. I kissed him deeply, "Bob, you are already inside me and I'm on the pill. Please keep going and cum inside me. Fuck me Bob, I want to cum on your cock."

Bob resumed pumping his cock in and out of me.

I could feel another orgasm building inside me. "Fuck me harder. I'm close to cumming." My body shook with my second orgasm of the night.

Bob grunted emptying his balls into me. We both collapsed on to the bed.

I kissed Bob and told him that I need to go. I cleaned up in bathroom, and dressed. When I returned to the room, Bob was standing by my room service tray counting money. He added another pile of money equal to the six hundred that was already on the tray.

"Thank you for a special night. Our conference ends tomorrow and I have one more night here at the resort. Could I talk you into another room service tomorrow night?" Bob asked.

"I would like that. I will keep my schedule open. Just contact Lisa for room service."

Bob grabbed my arm before I got to the door. "If I paid you $2000 would you consider spending the night with me?"

I looked Bob in the eye. "I'm not sure I'm supposed to, but I guess if I don't tell, no one will know. Can I let you know tomorrow?"

"Of course." Bob kissed me on the cheek as I left his room.

When I got back to my room I pulled out the money and counted it. Bob had doubled the money giving me 12 one hundred-dollar bills. I jumped in the shower happy with the money I had earned, but feeling stupid for not using a condom.

I reported for work as usually and Lisa quickly pulled me aside. "Wow, did you make an impression on Bob. He wants room service again tonight but only if it is you. Are you up for another room service tonight?"

"Sure, Bob is a nice guy. He was happy with his room service then?" I asked.

"Oh yeah, he went on and on about cute and sweet you are. He did apologize for going a little over time. I told him that was strictly between you and him. I want you to know that you are free to stick with the original agreed upon time but if you agree to go longer the client should pay. Did he?"

"Yes, he paid me extra for staying later. I was a little worried that was against the rules."

"No, that is fine. If the client wants something extra, you can do your own negotiation. You can always say no. Bob has put his order in for 9:00pm again so be ready."

I followed the same routine as the night before. On my last break, I went to my room and put on my lacy black bra and pantie set. I wished I had something different but figured they wouldn't be on long anyway.

As 8:45 rolled around, Lisa did her room service production. I grabbed the tray and she handed me a packet of condoms, which I put in my purse.

I made my way to the second-floor bathroom to apply my lipstick and I put a little hint of perfume in my panties and bra.

Tonight, I knocked on room 212 with confidence announcing room service.

Bob answered the door with a big grin on his face. "Sir, is this what you ordered?" I held out the plate with fruit and condoms on it.

Bob took the plate from me and looked me up and down. "It sure looks exactly like what I ordered, but I should examine it thoroughly. Did you think about my proposition for the night?"

I looked at him and smiled. "So, it is $2000 for me to spend the night with you right?"

Bob nodded counting out twenty one-hundred-dollar bills. I could tell he had more in his wallet.

I picked up the condoms. "I'm not supposed to, but for five more of these we can leave them in their package."

Bob smiled, counting out five more hundred-dollar bills. I put the cover over the plate with $2500 and grabbed Bob.

We kissed for several minutes till I pushed back. I put my arms out. "I believe you said something about an inspection."

"Oh yes, let me get to that. I should frisk you for weapons first."

I patted the tent in his pants. "It appears your weapon is fully cocked."

"We will get to that." Bob walked around behind me running his hands over my body. Feeling my tits and ass. "It all feels great, but I need a closer inspection. This blouse needs to go." Bob unbuttoned my blouse and tossed it to the floor. "It wouldn't be a thorough search if I didn't look under this skirt," said pulling my skirt down.

"Sir, I'm going to have to stop you there. I'm just here to deliver room service. If you take any more off, my privates will be showing. I'm not allowed to show my privates while I'm working. What kind of room service did you order sir?"

Bob unhooked my bra letting it fall to the floor. "I ordered the most beautiful woman in this place to spend the night with me."

I slipped my panties off. "Hotel rules instruct me to accommodate the guest's requests. I am required to check for weapons and this thing feels cocked and ready to fire." I grabbed his crotch and kneeled in front of him. "This is going to have to come out."

Bob quickly pulled his pants and underwear down, exposing his hard dick. I quit talking and started sucking. Bob simply moaned as my red lips surrounded his cock. He lasted longer than I thought he would. My mouth was getting tired when he announced that he was close. He grunted loudly and filled my mouth. I swallowed his jizz and climbed onto the bed.

To my surprise, Bob climbed into bed next to me and I noticed he was still hard.

He saw me looking at his hard cock. "Oh yeah, I hope you don't mind, but I some of those pills to help a guy. They seem to work."

"So, you took some pills to keep your dick hard to fuck me over and over?"

Bob looked nervous for a moment. "Uh, yes I guess I did, sorry."

I climbed on top of him guiding my pussy onto his cock. "Sorry nothing. That just means we are going to be very exhausted in the morning, but very happy."

I lost track of how many times Bob came inside me and how many times I shook with orgasms. We did get tired and slept for an hour or two. The first time after I fell asleep, I awoke to Bob shoving his cock into me. "Mmm, those pills seem to be working. Fuck me hard, Bob."

We both woke up to the sunlight shining through the window. As I predicted, we were both exhausted. Bob's dick was limp, and my pussy was sore.

I had found out during the night that, even though Bob wore a wedding ring, he was not married. His wife had died five years ago in a car accident. He told me he couldn't bring himself to date but needed sexual relief. He was very grateful for my kindness.

We showered together and then got dressed. As I was about to leave Bob went to the tray and added an extra five one-hundred-dollar bills. "I know I shouldn't ask this, but could I give you my number and maybe have you come visit me for a weekend?"

"I will take your number and give you mine, but not promises." I kissed Bob one last time, picked up my tray and walked to my room.