I woke up just after noon. My next shift at the restaurant wasn’t till 4:00 pm so I stayed in bed a little longer. I pulled out the bag I kept next to bed to hold the money I had made in my new endeavor. I counted out the $4200.00 that I had made in the last two days. I thought I would feel dirty about the money, but I rationalized that I hadn’t forced Bob to pay me for sex. I actually felt better that he wasn’t cheating on a wife at home. I felt I was doing him a service by giving him a sexual release while adding to my school fund.

Later at the restaurant Lisa pulled me into the break room. “You made quite an impression on Bob, he came by before he left with an envelope for me and one for you.” She handed me a white envelope with my name on it. “We will be slow for the next couple of days till the next meeting arrives Tuesday. Are you going to be up for more room service when they arrive?”

I looked at the envelope that obviously had cash in it. “Yeah, I think I will be ready when you give me the word.”

Monday night the guests for the next big meeting started rolling in. It was a big tech company with a lot of well-off individuals checking in. A few made their way to the restaurant. I brought out my sweet innocent flirting that got me some nice tips on that night.

On Wednesday night, Lisa pulled me into the break room. “I’ve got a room service call for you and it is very important.”

“Sure, what makes it so important?”

“Do you remember the group you had at table five last night? Four guys, well dressed, the one who with the grey hair about 60. He is the president of the biggest company here and the one who will decide if they come back. He thought you were the cutest thing ever. You remind him of his daughter. He wants room service from you tonight.”

“His daughter? That’s a little weird, isn’t it?”

Lisa smiled, “Weird pays better.”

“I remember that table, they were quiet but tipped well. Sure, anything special about him?”

"First thing, on your way to his room stop at the bathroom and put your hair in pigtails. He may want you to call him daddy. I can’t tell you what else to be ready for but me may want to fuck you in the ass or me may want to sit back and just watch you masturbate. Either of them a problem?” Lisa asked.

“I suppose I can do that, I’ve never done anal.”

“I will give you some lube for your purse but don’t worry, he has a small dick. Oh, and don’t kiss him unless he asks you to. Just make him happy so he will bring the meeting back here next year.”

“Thanks for putting pressure on me,” I laughed.

About 8:00 pm Lisa announced I was going on a room service call. I was surprised because my shift didn’t end till 10:00. I whispered to Lisa, “I thought I was going after my shift?”

She whispered back, “Mr. Holland just called. He wants a turkey club delivered to his room and his special. He wants it now, and like I said, he is very important.  Remember the pigtails.” Lisa covertly slipped a tube of lube and packet of condoms into my purse. “Room 620, the big suite.”

I stopped off at the bathroom on the fifth floor because there wasn’t one on the sixth. I put my hair in tails, refreshed my makeup and lipstick. I pushed my tits up farther in the pushup bra I was wearing.

Using my cutest little girl voice, I announced, “Room Service,” as I knocked on suite 620. I recognized the man who answered the door from the restaurant. “Hi, I’m Emily. I have a turkey club special order from Miss Lisa.”

“Nice to meet you Emily, I’m Larry. Lisa sent you, right?” I nodded. Larry signed the room service ticket adding a $50 tip. “Please take the tray to the table while I get something to drink. Do you want something?” I quietly shook my head no. “I really can’t eat all of this, will you please join me?”

I sat down at the table next to him sharing his sandwich. He thanked me for coming, telling me that I was the cutest girl in the place. We made small talk till the sandwich was finished. Larry stood up reaching into his wallet. He counted out ten one hundred-dollar bills. “I guess we are ready for the special part of my order.  Is that enough?”

I put the cover on the tray with the money, “Yes, it is. What would you like me to do and where?”

“Would you please join me in the bedroom? I would like to sit back while you take that uniform off, but please leave the pigtails in.”

I followed Larry into the bedroom where he sat on the bed. I took my blouse and skirt off, trying to look shy but seductive. “Damn, you have a hot body.  What size are your breasts?”

I unhooked my bra and laid it with my skirt and blouse, “They are 32C, would you like to feel them?”

"Oh yes, very much.” He grabbed my tits with both hands and squeezed. “They are wonderful, please lose the panties now.” I quickly pulled my panties off and tossed them to the floor. I stood in front of him naked waiting for his next command. “You are so cute, go get one of those condoms. I’m ready to fuck that pretty little pussy.”

I grabbed the package of condoms, pulling one out as I walked back in the room. Larry was just finishing pulling his underwear off when I got back. Lisa was right about his cock size. I had only now seen four dicks before. Larry’s was the smallest. I hadn’t brought the lube to the bedroom hoping he was not wanting to fuck me in the ass. “Are you ready for me to put it on?”

“Oh yes, how do you want me to fuck you honey?”

I knelt down kissing his dick before I unrolled the condom. “Any way you want Mr. Holland, I’m here for you?”

“Come on sweetie, I’m going to put my cock inside you. Call me Larry. Would you mind being on top? I want those pretty tits in my hands while I fuck you.”

I looked up at him with his dick in a condom, “Lay back and I will get to riding you.” Larry moved to the middle of the bed and helped me on top of him. I guided his dick into my pussy while he grabbed my tits.

Larry moaned as I started bouncing up and down on his cock. “Holly shit, you feel great. Slow down I don’t want to cum too soon.”

I leaned down to whisper in Larry’s ear, “Mmm, your dick feels great in my kitty, Larry.” To my surprise Larry pulled my head to his, kissing me on the lips. I kissed him back, pushing my tongue into his mouth. It felt odd kissing a man who was older than my dad, but I blocked that out, concentrating on making my client feel good.

Larry’s lips moved back and forth between my lips and my nipples. He suddenly grabbed my tits hard and grunted. Larry pulled me down to him kissing me. “That was very special sweetie. Please take the condom off my cock before it spills in the bed.”

I climbed off of his now limp dick and took the slimy condom off. This was the first time I had ever removed one. I took it to the bathroom trash and threw it in. I sat back on the bed next to him, “We have more time if you want me to do something else for you,” I said, looking down at his soft cock.

"Swing that little ass over here, I want to taste your pussy.” I pushed my leg over Larry’s chest lining up my ass and pussy into his face. I moaned when Larry pushed his tongue into my pussy. He was quite good at eating pussy. I put my head down into Larry’s crotch, finding his cock right at my mouth level.

I kissed his dick a few times before letting it slip into my mouth. I sucked for over a minute, thinking his cock was going to stay soft. Larry let out a moan as his cock hardened in my mouth. Once his cock was rigid, I started sucking and stroking him hard. Larry had lost his concentration eating my pussy and was just now moaning as I sucked and stroked him.

When my mouth got tired, I stroked him while I rested my mouth. Larry was encouraging me, telling me he was close to cumming. I put his cock back in my mouth sucking him.  Larry grabbed my butt cheeks and grunted, shooting a load of cum in my mouth. I swallowed his cum and slid around lying next to Larry. Larry put his arms around me hugging me tight. “Honey, I haven’t cum twice in one night in twenty years.” Larry got up out of bed. “I need to get some sleep; I have to run the conference tomorrow.”

He handed me my clothes and walked me out to the kitchen area. While I got dressed, Larry counted out five more one-hundred dollar bills onto the room service tray. “Emily, we have a big banquet that is going late tomorrow, so I will be very busy. But, I would like for you to come back to my room Friday night. I will double this if you will.”

I kissed him on the cheek, “What time do you want me here?”

He handed me the tray, “I will have instructions sent to your room.”

The next day at the restaurant, Lisa congratulated me on a successful night. Larry had already told the owners that next year’s conference would be held at the resort. She offered to let me off for the night. She said it would be slow with the banquet in the main hall. I declined, knowing that most of the staff was working the banquet and the resturant was going to be short staffed.

I waited on a couple that appeared in their early thirties, both well-dressed and good looking. The woman clearly had work done on her breasts, they were huge. They were very friendly and talkative with me.

Close to the end of my shift, Lisa called me over. “I have a room serviced call that requested you, but you don’t have to go if you don’t want to. I know you have an important appointment tomorrow night. The call is a little different.”

“You’ve got my curiosity up. What’s different about it?” I asked.

“The couple you served about an hour ago, they are swingers.  They are wanting to play with you. The wife really liked you. Have you been with another woman?” I shook my head no. “You can say no, it will be alright.”

“I’m okay with new things, I think I would like to try.” I hadn’t been with a woman, but I was curious.

Lisa gave me a tray with a bottle of wine, three glasses, and some crackers. I knocked on room 310, announcing room service. The woman I had waited on met me at the door. She invited me in. “You ordered wine, crackers and a special?” I asked.

“Yes sweetie, Lisa sent you?”

“Yes mam, Lisa sent me for the special. I’m Emily.”

“It’s nice to meet you, Emily, I’m Tiffany. Richard, bring your wallet and meet Emily.” I put my hand out to shake Tiffany’s hand and she grabbed me, pulling me into a hug.

“Wow, she is a cute one. Sorry, I’m Richard. How much do we owe her honey?” Richard asked holding out his wallet.

“Six hundred, put it on the platter Richard.”

“A bargain for such a lovely young thing. Not to be demanding but I would love to see you two beautiful women naked in the bed.”

I looked at Tiffany, who was already pulling her dress off. I tried to catch up taking my blouse and skirt off. As I took my panties and bra off Tiffany was on the bed motioning me to her. She met me with a hug, then a kiss on the lips. We started making out with Tiffany’s hands squeezing my tits. I cautiously moved my hands to her big tits. I loved the way they felt.

I jumped when Tiffany stuck a finger in my pussy.  Her fingers hit my wetness, causing me to moan. Tiffany whispered in my ear, “Emily, I would love to taste you.”

I didn’t say a word,  laying back on the bed spreading my legs. She moved between my legs sticking her tongue inside me. “Oh God, that feels so good,” I moaned.

Tiffany continued to eat my pussy while I had forgotten about her husband. He made a noise causing me to look his way to find a large cock staring me in the face. I jumped again, Tiffany pulled her head from my pussy. “Honey, give her some warning before you pull that out.”

I reached out grabbing his cock, “Oh shit, that is big.” It wasn’t a mystery what Richard wanted me to do. I adjusted my body on the bed to reach his cock with my mouth. He let out a little moan when I started sucking him.

Tiffany looked up again from my pussy, “Richard, I know you are loving getting your dick sucked but you should taste this pussy. It is so sweet.”

I released his cock so he could move between my legs. Tiffany scooted up next to me kissing me while her husband ate my pussy. I was having a hard time concentrating on Tiffany, with her husband tonguing my pussy.

“Honey, put a condom on. I think Emily is ready for you to fuck her.” I nodded to Tiffany as she kissed me.

The next thing I knew was Richard climbing on top of me. He kissed me and asked me if I was ready. I grunted that I was. His cock pushed against my pussy lips. Richard slowly pushed his cock inside me. “Wait for her to get used to your size, honey. I don’t think she has had one your size.” Tiffany said.

I nodded to her but told Tiffany her husband felt great inside me. Richard started slowly pumping my pussy. “Damn, she is so tight. I hope I can make her cum before I do.”

Tiffany played with my tits and said, “Pump her hard honey, I think she is close.” Tiffany was right, my orgasm was just about to burst.

My body shook hard from the big cock inside me. “Fuck yes, that’s it.  I’m cumming.”

Richard kept pounding till he grunted, filling his condom. “She’s incredible Tiff. Emily, have you tasted another woman?” I shook my head no. “Tiff, let her try you. She might like it.”

Tiffany spread her legs, giving me her access to her shaved pussy. I have had my pussy eaten enough to think I knew what to do. I started kissing and licking her. “Mmm, I like the taste,” I said into her pussy.

“For your first time you’re doing great sweetie. Keep going, I want to cum, too.”

Tiffany’s juices started to flow the more I licked and fingered her. I felt Richard behind me lifting my ass up to be on my knees. His fingers probed my pussy causing me to wiggle as I ate his wife’s pussy. My juices were flowing just like his wife’s when Richard removed his fingers.  I thought he removed his fingers to watch his wife cum.

I was wrong, Richard was simply putting a condom on before he shoved his cock into my pussy. “Oh fuck,” I said pulling my head up from Tiffany’s pussy.

“Honey, you should warn her before you put that in her,” Tiffany said.

“No, it feels good. I just want to make you cum.”

“Keep going, you are close sweetie,” Tiffany moaned.

It was hard to focus on her pussy with a big cock in me, but I kept licking.  Tiffany pushed my head into her pussy announcing she was cumming.

Tiffany slid out from under me to lay next to me, kissing me as her husband fucked me from behind. Having already cum once, he lasted much longer this time. I was cumming for the second time and he was still going. I was having a hard time staying up on my knees when he finally grunted, cumming in his condom.

Tiffany kissed me on the lips, “That was incredible sweetie. Richard, you put a couple more hundreds on that platter, she earned it.”

I quickly got dressed picking up the platter. Richard and Tiffany met me at the door, both giving me a kiss thanking me again. I got to my room jumping in the shower. When I got out, I noticed there was a box on my little table. Inside the box there was a little school girl outfit, plaid skirt and white shirt. Underneath that was a pink bra and thong. Digging deeper I found a pair of white hose. The last thing left in the box was an envelope. Inside I found a room key, ten one hundred-dollar bills and a note.

“Please be in my room by 9:00 pm dressed in the enclosed clothing. At all times please call me ‘daddy’. Consider the enclosed a down payment of further compensation.”

Already naked from my shower I tried on the outfit. It fit perfectly, I guess Mr. Holland does his research well. Looking in the mirror, I looked like your typical school girl from a porn movie. A little red lipstick and my hair in pigtails will complete the look.

The next day at the restaurant, Lisa called me into the break room. “You got the package?” I nodded. “I want you out of here no later than 6:30. Get a shower and make sure you’re dressed and ready for him when he is done with his meetings. You’ve done great so far. He couldn’t stop talking about how cute and sweet you were. You apparently look a lot like one of his daughters. That fact is going to keep him out of your ass, but he wants you on top of him again. Be very obedient, he is going to want you to ask him to fuck you.”

“That’s kinky, I guess it is worth it.”

Lisa laughed, “Damn right it is, the owner had given me a big bonus for the conference coming back. You will get a nice portion of that. I saw how much was in the box and I bet he will double that.”

“Now I’m nervous, I might blow this.”

“Honey, you blow him and we are all good.”

I worked my shortened shift and left for my room. The warm shower felt good before I put on my makeup. I decided rather than traipsing through the hotel in a school girl outfit, I would get dressed in Mr. Hollands’ room. With his box under my arm, I quickly made my way to the sixth-floor suites. Using the key from the box, I entered the room with nobody watching. I got dressed then placed a few condoms on the night stand along with the tube of lube. I sat down on the edge of the bed and waited for “Daddy.”

The clock read 9:30 when I heard the door open. I jumped up, rushing to the door. Larry tossed his suit coat on the love seat and started to undo his tie.

“Hello Daddy, how was work?” I asked in my best little girl voice.

“It was very good honey, how was your day at school?”

“It was good but Daddy we had a class on sex education. It was very confusing and the boys were making fun of me because I didn’t understand it. Can you help me?”

“Of course honey, boys and girls have different parts. When a boy and girl like each other they put their parts together to try and make a baby. I have a penis and you have a vagina. The boy puts his penis in the girl’s vagina, it is supposed to feel good when they do.”

“Daddy, what does a penis look like? Will you show me?” I asked, getting on my knees.

“Because you asked and need to learn, I will.” Larry pulled his pants off and removed his briefs.

I reached out and gently touched his cock stroking it lightly. “It is so pretty, Daddy. Is it always this hard and rigid? I bet it is hard to walk around like that.”

“It only gets like that when it is happy. Your touching is making it happy.”

I continued to stoke the cock in front of me. “Daddy, if I’m making it happy. That means it likes me. Would you show me what it feels like to go in my vagina?”

“I guess you need to know, but you can’t tell Mommy. Take you school uniform off but leave those stockings on.” Larry took his shirt off and got on the bed while I got naked. He put a condom on and summoned me to get on top of him.

“Oh Daddy, my girl thing is wet and tingly. Does that mean it likes your penis thing?”

“Come up here and sit down on it. We can see how much your girl thing likes my penis thing.”

I moved up his body lining my pussy up with his condom covered cock. Playing his little girl had gotten me excited and my pussy was wet and tingly. I moaned loudly as Larry’s cock slid into me. “Oh Daddy, your penis does feel so good in my girl place. What do I do now?”

Larry groaned, “Just start bouncing up and down on me.”

I did as he said grinding my pussy into his cock. Larry reached up, fondling my tits. I leaned down to his ear whispering, “Daddy, are you fucking me? It feels so wonderful.”

Larry held me tight and grunted. He had just filled his condom. “Yes honey, I just fucked you and it was wonderful. Roll off of me and spread your legs I want to taste that sweet pussy after I take this condom off.”

Larry quickly shed his condom, getting between my legs licking and fingering my pussy. Larry took his time eating my pussy. As I was getting close to my climax, I was thinking to myself that he was paying me to cum. “Yes, Yes, Oh Daddy you’re making me cum.” I called out as my orgasm over took my body.

Larry crawled up my body to kiss me on the lips. His tongue pushed into my mouth as he laid on top of me. To my surprise he was hard again and pressing his cock against my pussy lips. Still in character, I said, “Daddy, your thing needs to be covered before it goes back inside me.”

Larry used my name for the first time all night, “Emily, I will pay you triple if you will allow me to fuck you without a damn condom on. I want to feel my cock in your sweet pussy without a bag on it.”

I knew I shouldn’t, but the money was too much to pass up. I push my hips up to his cock pressed against my pussy lips. The head of his cock slid into my slippery pussy. Back in character I moaned, “Fuck me Daddy, I want to feel you cum inside me.”

Larry pumped me hard, all the while kissing me and whispering in my ear how great my pussy felt. He lasted longer than I thought he would, but he finally grunted that he was cumming. He collapsed on top of me after shooting his load. He rolled off of me out of breath and completely exhausted.

We lay on the bed catching our breath for a few minutes when I decided to slip into the bathroom to clean up. I took my time wiping out the cum and taking a pee before returning to the room. I wasn’t sure if we were done or Larry would want to have more sex.

When I opened the bathroom door Larry had his underwear on standing by the table counting money onto the table. Larry motioned me over to him. He handed me my clothes letting me know I was done and needed to get dressed.

Larry handed me an envelope he had put the money in. “Thank you for a great night, Emily. I hope you will find what I put in the envelope enough. I have also put my card in there. Lisa told me you are doing this to get money for college. I want you to call me next week for two reasons. I have several contacts with scholarships and grant providers who can also help you. Second, I have a ranch I would like to invite you to for a little job.”

I took the envelope then kissed Larry on the cheek. “I will call you next week.”

“Holly shit,” I thought to myself when I got back to my room and opened the envelope. In the envelope was $5,000 in one hundred dollar bills. I pulled out the card and put it in my wallet. I smiled and thought to myself that I would in fact call him next week.