Nicole Cashes In

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Desperate for money, Nicole takes the plunge.
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*****

I was staring at the beer in front of me, waiting for it to give me the answer. If it had the answer, it was being surprisingly tight-lipped. I had already checked with three of his friends and all of them were equally silent.

The bar stool where my butt was planted was located in Jerome's, a seedy little neighborhood bar that caters to a mostly male clientele and the occasional transgender person. That would be me. My name is Nicole and I'm working on being a she.

I've been taking hormones for over two years and living as a woman for the last year. From outward appearances, I am a mid-30's woman drinking in a gay bar. I have been coming here for a while, not for the sex, but because I'm usually left alone. Normally men interpret a woman alone in a bar as someone who wants to be picked up. Not that I'm averse to that, but sometimes I just want to drink.

Ron, the bartender, drifted my way. "Nicky, you seem more intent on gazing at that beer than drinking it. What's up?" Only my family and Ron call me Nicky.

"Problems are usually either about sex or money and this time, its money. The other day the check engine light came on in my car. I figured it was some kind of sensor, probably around a hundred bucks, throw in another hundred or so to put it in, I'm set. Instead, we are looking at two catalytic converters, four oxygen sensors and enough time to build the Ark. So now we are well over three grand and climbing."

"Ouch! That hurts."

"Tell me about it. You own a car, crap like that is going to happen. I understand that." I paused to take a drink. "But honestly, that isn't the real issue. I have been thinking about getting my boobs done. I have gone back and forth for a while and finally decided to go ahead. I took some vacation next month, scheduled the surgery and have the money all tucked away in the bank, waiting for the big day. Now it's all out the window." I looked up from my beer. "So tell me, what do you think of women with small tits?"

He chuckled at the last part. "I don't care too much about the size of the rack, more of an ass man, but I really like my women to have an actual pussy. No hard feelings." He stopped cleaning glasses, turned around and grabbed a bottle of Jack Daniels. He filled a shot glass full, sat it in front of me and went to the other end of the bar to wait on another customer.

When he came back he began cutting up limes. "How desperate are you? What would you consider doing for money?"

I really didn't know how to answer. The questions caught me completely off guard. "I thought you only wanted pussy?"

"There's this guy that comes in occasionally, asked me if any women such as yourself, or as he puts it 'girls with a little extra', frequent the bar. He said he is looking to party and he can be generous. He is always flashing a big wad of cash. He's not particularly attractive but he is not a troll either."

I've done it for lots of reasons but never for money. "Did he mention what this 'party' might involve or how 'generous' he might be?"

"He didn't go into detail but I think you have a general idea. I'm sure he wants more than a kiss." He sounded a little pissed. "Listen, normally I wouldn't even have brought it up. I'm not in the business of solicitation but you seem to be in dire need of cash so I thought I would mention it."

"Sorry, Ron, I realize this is awkward for you. It's not something I ever considered but I really don't want to postpone my plans. When does this guy come in?"

"No real schedule. He isn't one of the regulars. As I remember, it's usually later in the evening. If you're interested I could text you the next time he drops in?"

"Okay. I need to think about it. But I'll give you my number, just in case."

I finished my beer, lost in contemplation. Was this what it had come to, me selling myself? It would solve my immediate problem but did I really want to go down this path? There were so many thoughts swirling around inside my head that ordering another drink no longer sounded appealing. I paid my tab, bid Ron adieu and headed home.

********************

It was several days before I got a text from Ron saying Mr. Moneybags had arrived. I had thought about it off and on but hadn't really settled on an answer. I decided it wouldn't hurt to meet him and see what he had in mind.

I rummaged through my closet and pulled out a red dress. It was shorter then I would normally wear and rather low cut. I had worn it once on a date and although my companion seemed to enjoy it, I had felt somewhat exposed. On went a pair of pantyhose and I found some 3" pumps in the back of the closet. I must admit I was overdressed for where I was headed but I looked the part of what I was supposed to be. I sat down and put on my makeup, paying extra attention to my eyes. Nothing says lady of the evening like heavy eye makeup.

I walked into the bar and all eyes turned my way. As I mentioned, I'm a regular here but not dressed like this. I headed toward the bar. "My goodness girl," Ron said, "you are smokin'. I might have to revisit that requirement of having a pussy." He paused to ogle. "He is in the back...last booth."

As I walked back, I heard a few "oh baby" and "hot stuff' from the other patrons. While approaching, I looked him over. He appeared to be average height (hard to tell sitting down) and he was a little on the pudgy side. He had thinning hair and black-rimmed glasses, which framed small, close-set eyes. My guess was he was in his late forties. I stopped at the table and said, "Mind if I join you?"

He looked up from his phone. He seemed to be surprised that someone was there. "Please do. Would you like a drink?"

"It's a bar isn't it?" After I said it, I wished I hadn't. I sounded a little bitchy. He didn't seem to notice.

"You are correct, it is." He waved at the waitress.

"I'll have a White Zinfandel," I told her. I decided to drink like a lady.

"To whom do I have the honor of addressing and why would you like my company?"

"My name is Nicole. The bartender thought we should meet. It seems we might have something in common. Outwardly I look like a woman but between my legs I have something very unladylike and I hear that might be of interest to you."

"Hmm, I'm already interested. You are a stunning lady. What else did the bartender tell you?"

"He did mention that there might be some monetary remuneration involved for unknown services."

He laughed. "Yes, exactly right. Since you are here you are probably wondering what that might involve and what you can expect in return." He continued on without waiting for me to answer. "I find it thrilling to be with ladies such as you, so beautiful and feminine but with a big surprise." There was a wicked gleam in his eyes. "You can count on oral and anal sex, some bondage and whatever else I feel like. I totally call the shots and all of it will be done under a role-playing scenario. Not to worry, there will be nothing too debasing. I will not be sampling your wares, but if you feel the need to pleasure yourself, I may allow it"

The open-endedness of it left me a little worried. But he hadn't mentioned anything that I hadn't tried before.

He continued on, "For this, I will give you a gift of $2500, maybe more if I like the way you perform. How does that sound?"

"I'm in a money crunch right now or I wouldn't even be here. So is this just the two of us or are there more players?"

"Why? Do you like a crowd?" Before I could answer, he continued. "No, it will just be the two of us. Maybe if it goes well, I could organize a conga line for you."

"I don't think that will be necessary. How soon do you want to do this?"

"You are so lovely; I wish it could be tonight. But it will probably take you a few days to get the proper attire. You can let me know when you are ready."

I sipped my wine and thought about his proposal. I really could use the money and as long as he wasn't going to crap on me I could probably put up with most things he could deal out. Hell, normally a good meal will get my date at least a blow job, so why not cash in? Plus I told myself, it would just be this one time. "Okay, let's do this. What do I need to do?"

He pulled a small notebook out of his jacket pocket and began to write. When finished, he tore out the page. He then reached into his pants pocket, pulled out a money clip that was overflowing and peeled off a $100 bill. "Go to a uniform store and buy a hotel maid's outfit. I'm not talking about those sexy French maid outfits, just a regular hotel maid. When you have everything together, text me and I'll tell you where we will meet."

He handed me the note, money and a business card. All it had on it was Jeremy Starnes and his number. The note read:

Hotel maid uniform

White cotton panties - any style

White cotton bra

Pantyhose - taupe/suntan

White shoes - not heels

He took a drink while I read the note. "Any questions?"

"No, everything seems pretty straightforward. I'll let you know when I get everything together."

"Perfect. I will be awaiting your text." He picked up his phone. I could tell we were finished. I emptied my glass in one gulp and got up to leave.

I had spent a fair amount of time getting all slutty, I really hated to waste it. I noticed a young guy sitting at a table by himself. I went over and sat down. "Hello. I couldn't help but notice you, such a handsome, hunk of a man, sitting here all alone." My hand began rubbing up and down his inner thigh. "Not finding the right guy? Believe me, I understand. I have that trouble all the time." He was having trouble sitting still but at least he hadn't made me move my hand. "I'm hoping tonight isn't one of those nights. I really could use some action from a strapping, young buck like you."

"Ma'am, all this attention is flattering but I'm strictly gay," he said

"Ma'am isn't that darling. Don't worry, Strictly Gay; I'm not going to ask you to stick your dick in some vile, cootie-filled vagina. What I am going to do is go to the ladies room, freshen up my make-up, and hope you join me."

I stood up and headed for the restroom. As I walked away; I added a little extra sway to the hips. If he still had any interest in women, I hoped that would seal the deal.

Looking in the mirror, I touched up my make-up, put on some more lipstick and checked out my hair. Time seemed to drag. I had decided he wasn't going to show when there was a light rapping on the door followed by him slipping in. Looks like my lucky night.

With one hand on his shoulder, I backed him up against the door and gave him a big, passionate kiss. My other hand was rubbing across the front of his pants, finding his erect manhood just below the fabric. It appeared women still excited him. I squatted down, frantically began to undo his belt and then unzip his pants. Pulling his Jockeys down, I was greeted by the most luscious hard cock. I immediately grabbed it and guided it into my mouth. He muttered "Oh, lord" as I began sucking it, my tongue licking whatever it could reach. My head was bobbing back and forth, taking him in deep. He was moaning like a young girl when she first discovers the pleasure of playing with herself. I paused the sucking and took time to lick his balls. I had his entire sack in my mouth, massaging it with my tongue. But what I really wanted was that cock so I cut the ball game short. I slid him back into my mouth and began the old in and out, building toward liftoff. It wasn't long before I could feel him starting to tense up. My free hand cupped his balls; they were pulled up into tight little nuggets. He suddenly grabbed my head and buried his cock deep. I can never get enough cum and he didn't disappoint. He just kept squirting and squirting, each spasm filling my mouth with his delectable, hot goo. I thought he was never going to stop. I swallowed the first batch. Then I used my tongue to coax the rest of it out.

I stood up and gave him a semen soaked kiss. "Mama thanks you for that, just what I needed. Now, why don't you head on back, honey, before we both are missed?" I was just trying to protect his reputation, mine couldn't be helped.

"Okay. Thank you ... ma'am." With that, he got himself tucked away and was out the door.

While I waited, I made sure I was presentable. When I came out, he was over in the corner, playing pool. As I headed for the door, I caught Ron's eye, I put my finger up to my mouth to say 'shh' and then blew him a kiss.

*************************

Between the issues with my car and work, it was several days before I could deal with the maid's uniform. I searched online and found a store not too far away that looked like it would have what I needed. Once there, I picked out what I would consider a regular hotel maid's dress. It came to just above the knees, was light yellow, a white collar, and white trim around the sleeves. It zipped up the front. I already had a pair of white canvas shoes that I figured would be fine. A stop at Target and I was set with everything else.

That evening I sent Starnes a text letting him know I was ready. It wasn't too long before I received a reply asking if Wednesday evening would be good. That was several days away. Part of me wished it was sooner so I wouldn't be questioning my decision so much... I let him know that Wednesday would be fine.

I was to check in to the Hanover Hotel on Kingshighway by seven o'clock. There would be a room reservation for Nicole Sheridan. In the room, there would be further instructions.

*************************

Wednesday was a terrible day, one crisis after another. There was little time to think about the upcoming evening plans, which was a good thing. Luckily I had packed a small bag the night before that had everything I should need in case I got out of work late.

The hotel was an older hotel that has been part of the city's history for quite some time. It was very stately and elegant. I wondered how much the room was costing him. But it was his money and his fantasy. The room was waiting just as he said.

When I got in the room, I threw the bag on the bed. The room was small but it wasn't like I would be spending much time here. I noticed on the dresser there was a typed note.

Get dressed - your make-up should be modest, you are a hotel maid

Text me when ready - wait five minutes

Bring several towels - come to room 415 (next door)

Knock on the door - announce yourself - door will be unlocked

Enter - I will appear from the bathroom

You will turn away but keep stealing glances

Interested but reluctant - eventually you will engage but withdraw

That was all that was written. It sounded like a very short session.

I proceeded to get dressed and applied my 'modest' make-up. I sent a message that I was ready and waited the prescribed five minutes. Then grabbing several towels from the bathroom, I headed for the door. I was a little worried that I might run into a real maid but at this time of night, the chances were slim.

I noticed the door was slightly ajar. I knocked and pushed it open. As I entered, I observed that this room was much larger than mine. There was a seating area off to the side with a desk and several chairs. Unsure of what exactly I was supposed to be doing, I said, "Maid service. Here are the extra towels you requested."

From the bathroom, I heard, "Bring them in and put them on the dresser."

I did as I was told. As I turned from the dresser, he walked out of the bathroom. I almost gasped. There stood the pudgy man I had met in the bar, naked, with at least seven inches of rock hard cock. I was so impressed; I couldn't stop staring. Remembering I was not supposed to look, I turned away. "I'm sorry sir, you caught me by surprise," I said apologetically.

"That's okay, my dear. Did you like what you saw?"

"Please sir, it was an accident." I kept my back turned but casually took a peek.

He started walking toward me. "I'll take that as a yes. Why don't you touch it? I don't mind."

"No, sir. It is against hotel policy. I could get fired."

By now he was about six feet away. "You know you want to. Who is going to know? I certainly won't tell. It will be our little secret. There could be a big tip for you."

I wanted to grab it and stuff it in my mouth but I needed to stay in character. Although the note did say I was supposed to 'engage'. Nervously looking around the room, as if someone else was there, "Well, maybe just a touch." I turned and walked toward him. I reached out and wrapped my hand around his swollen member. It was difficult to contain my excitement as I began sliding my hand up and done his hard shaft. Suddenly I stopped and pulled away. "I can't, sir. I don't want to lose my job." I turned and began to walk toward the door.

"Wait a minute." He walked over to the desk where there was an open laptop. He punched a few keys and then turned it around so I could see it. There was a video running of what had just transpired. "When I get done editing this, it will appear like you came on to me. I'm sure the hotel management will not take too kindly to their maids propositioning the guests. Now come back over here and continue what you started."

Now I understood how this was going to play out. I walked over to him and begin to stroke his big cock.

"So tell me pretty lady, what's your name?"

Nervously I answered, "Nicole."

"That's a pretty name for a hotel whore. Why don't you get down on your knees and suck it for a while?" When I didn't react quick enough he added, "Remember the video. You could be out of work before the evening is over"

I got down on my knees and took the tip into my mouth. My tongue began licking all around it. I know this was supposed to be against my will but I was loving it. I could imagine myself sucking his cock all evening. I held the base with one hand and I was taking in all I could.

"My, my, such a good cocksucker. I'm surprised you were so reluctant. It's obvious I'm not the first male guest you have given 'maid service' to. That's good. Take it all in." He grabbed the back of my head and shoved his dick deep into my mouth. I gagged as I gulped for air. He held it there for just a few seconds and then gave me a reprieve. Then it was back in again. He had a nice rhythm going when suddenly he pulled out. "Let's slow down, slut. You didn't think you were going to get off that easy, did you? A swift suck and you are done? You are mine for as long as I want."

"Please sir, just let me do this quickly. I really need to get back to work. They will be looking for me. I could get fired," I pleaded.

"Honey, when they see the video you will get fired so you may as well take your chances with me. Stand up, whore. I think we should give your mouth a rest." He went over to his suitcase and returned with a ball gag and what looked like strips of leather. "Now turn around so I can get this on. Open your mouth wide." He placed the ball in my mouth and secured it. "Now put your hands behind your back." He took my hands and bound them together.

"There. Now you won't be going anywhere. Let's see what we have in here." He unzipped my dress to my navel and then pulled it down so it was about halfway down my arms and my chest was exposed. "Such a plain bra. I guess you save the lace ones for the paying clients." He began fondling my breasts. "Very nice! Small but firm. And I see someone can't hide their excitement. Your nipples are telling on you." He was pinching and squeezing my nipples. "Maybe they should be taught a lesson." He reached around, unclasped my bra and lifted it up so that they fell out. Then he went back to his suitcase and came back with nipple clamps. He put one on and I screamed. The pain was intense. "Don't worry, you'll get used to it." He then put the other one on and I thought I was going to die. I tugged at the restraints but that was a useless endeavor.

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