"Hey, it's my turn," I protested.The clatter of dishes during the noon-hour rush filled the air as bus boys and waiters scurried around the popular restaurant. Tom and I had spent almost an hour talking about the internet and the growing online industry in between updates on our jobs and friends. The waiter refilled our coffee and laid the check near Tom before he left. When I reached for it, Tom grabbed it from my hand.
"Hey, it's my turn," I protested.
"No way." He pulled a few bills out from his wallet and placed them on the tray with the bill. "It's well worth a lunch just to pick your brain on all this new technology. I can never keep up with it."
"No one can keep up with it, Tom. It's crazy. Pretty soon we'll all be specialists in our own little niche and no one will understand the big picture any more."
"Well, it's my treat anyway. How often do I get to have lunch with a sexy woman?"
I rolled my eyes and ignored his remarks. Tom was often a consultant for our company and I had tried to maintain our professional, yet flirtatious friendship. Most of it was in jest, but there was always a part hinted at the possibility of a repeat experience we had shared.
We had gone to work-related party at a private home, and late into the evening after several drinks, a few of us took advantage of a naked plunge in the big redwood hot tub. Before long, it was just Tom and I, and he kept flirting with me and talking about how he always wanted to do it in a hot tub. When he sat up on the edge of the tub to cool off, he revealed his hard cock. I couldn't help but stare at it as it jerked from my attention. I'm not sure why I was so moved by the moment, but I slowly floated over toward him, and without saying a word, took his cock in my mouth.
He was anxious about getting caught and occasionally looked over his shoulder to the house where people were still gathered. Within a few moments, and almost silently, he came in my mouth, just as a new group headed out the door and in our direction. I slowly floated back to the other side of the tub as they approached and then left shortly afterward without seeing Tom again that night. He had never let me forget it.
"So what else is new?" asked Tom, bringing me back to the moment. "Been hot tubbing lately?"
I smiled and winked at him. "It wouldn't be the same without you."
He shook his head as he sipped his coffee. "Man, that night took five years off my life."
"No, I'm pretty much all work and no play these days," I complained. "I can feel the stress building inside of me. The only fun I have are my fantasies on the long drive home."
"You have Fantasies?" Tom looked confused.
"Sure, don't you?"
"Just the one about hot tubbing with you again," he laughed.
"Yes, another moment of weakness in my life."
"So, what's your fantasy?" asked Tom.
"Oh, I don't know..." I sipped my coffee and looked around the room. Some things were best kept to myself.
"Come on. Indulge me," he pressed.
I leaned over and lowered my voice, not wanting the few remaining patrons to hear my confession. "Maybe it's because I'm working so hard, but I would love to like... have sex with someone and get paid for it. You know, like a hooker."
Tom reached into his jacket and pulled out his wallet. "How much?"
"Stop it," I laughed. "I was being serious."
"Hey, so am I!"
"Well, that's not the fantasy, Tom. It has to be with someone I don' t know, which is why I could never do it. I would never have sex with someone I didn't know. It's just a fantasy."
Tom stuck his wallet back inside his jacket and thought about it. "I see what you mean. But what if it was safe. Would you do it?"
"What do you mean?" I asked.
"Well, what if one of your friends arranged it?" He winked at me and raised his eyebrows mischievously.
"Oh, turning into a pimp now?" I laughed at his suggestion.
"Hey, maybe it's my fantasy too!"
"Yeah, right!"
With both sat quietly and drank our coffee, grinning as we watched each other ponder the idea. Even if it was someone Tom knew, I still couldn't have sex with someone I didn't know. It was just a fantasy. Something that happens in the dark recesses of the mind.
"I know plenty of guys who would be willing to pay for you," encouraged Tom.
"I couldn't do it, Tom. It's just a fantasy," I insisted. "I could never have sex with someone I didn't know pretty well."
"You could give them a blow job," he laughed.
I grinned and looked away, thinking about the possibilities. In all reality, I could probably do that.
"What do you think a blow job goes for these days?" asked Tom.
I shrugged my shoulders. "I wouldn't have a clue."
"I would say at least $100 bucks."
"Are you serious?" I asked in disbelief.
"For your mouth? You bet."
"Wow..." The thought of some guy paying me $100 to suck his cock felt exciting.
"Of course there would be the matter of my finders fee..."
"So this is a two for one offer, huh?" I laughed. "Already my rate is dropping."
"Hey, you know what?" Tom leaned over closer, the look of excitement in his eyes. "I've got this crazy client, Mike, in town this week. He's always talking about wanting to get something on the side. He would be perfect!"
"Tom, you're crazy!" I protested.
"No, I'm not. He'd be perfect."
"What do you expect me to do? Show up at his hotel? I don't want anyone to know who I am; I've got a reputation and a career... remember?"
"I won't tell him who you are..."
"Look," I said, grabbing my purse and pushing my chair back. "I have to get back to work." Tom rose and walked beside me as we headed toward the parking lot. He wouldn't let go of the idea, and as we reached my car, he continued with his plan.
"Let's meet tonight down by the waterfront. Somewhere dark. No one will know."
"I'm going to a fund-raising dinner tonight for a friend," I answered, opening my car door and turning back to him.
"Perfect. We'll meet you after the dinner."
"You won't give up on this, will you?"
"Hey, I'm just trying to help you fulfill your fantasy." The mock of innocense was comical.
"I'll think about it," I offered.
"Just call me. I've got my cell phone on."
"Okay," I said, climbing into the car. "Thanks for lunch."
"The pleasure's been all mine."
I hurried back to work and tried to forget about the crazy scheme Tom had brought up. I should have never shared my fantasy with him in the first place. It was just taking the teasing a bit too far. Around three that afternoon, I got an email from him.
"Hey. Guess what? Mike says he'll pay you $100 to meet us tonight. How about it?"
My heart jumped when I read the message. I couldn't believe he actually asked the guy if he wanted a hooker... or a blow job... or whatever he had asked him. Maybe he was just bullshitting me. There probably wasn't even any client named Mike. He was probably just hoping I would show up and do him again.
I hit the reply button and typed in my response: "Where?"
I laughed as I hit the send button and went to my next meeting. By the time I returned to my desk it was after four. There was a reply from Tom.
"Take Hanover street all the way down to the harbor. There's a park facing the water. We'll be sitting in my car at the end in the parking lot where it's dark. What time?"
I sat there and thought about the whole idea. The harbor was relatively close to the fund-raising dinner. But could I do it? I hit the reply button and started my response.
"Okay. Here's the deal, Tom. I'll show up at 9:30. Your friend will be in the back seat of your car, behind the passenger seat... blindfolded. I don't want him to see me. I also don't want him to touch me, except maybe my hair. Have him put the money on the back dash. When I arrive, you come and walk me to your car. After I get into the back seat, you either get in the front seat or stand next to the car. (I don't want to be left alone with him.) When we're done, you walk me back to my car. Tell your friend not to remove the blindfold until you return."
I read the message over and over, and then as if pushing myself over a cliff, I hit the send button. There was a big part of me that really wanted to do it, but I was nervous and afraid that something might go wrong. What if I changed my mind? What if they did? I sent another quick message.
"Page me if you change your mind. I'll call your car phone if I change mine."
I changed into a black cocktail dress for a dinner party. The fund-raiser was for a political candidate I was supporting. Most of my contributions came in the form of volunteering my time on the phones or helping with the computers, but tonight I was schmoozing with the financial contributors.
Any thoughts of my late-night appointment were put aside after I reached the party. The loud music, colored balloons, rich food, stiff drinks, and fast talkers kept me on my toes. I was surprised to find that most of the men wanted to dance more than talk about the issues of the campaign. But at least when we did talk, we had something more interesting to discuss than my astrological sign.
As the night wore on, I started checking my watch more frequently. Even I didn't know if I was going to meet Tom and his friend. At nine, I went to the ladies room to check my makeup. I looked at myself in the mirror and shook my head.
"Girl, what are you thinking about doing?" I said out loud. I bent over and checked my cleavage in the low cut dress. "You're certainly dressed for the part." I freshened my lipstick and then headed for the coat check room. Moments later I was driving down Hanover street toward the harbor. I could feel my heart beating in my chest and the wetness already gathering in my panties.
When I pulled into the parking lot, I saw Tom's car parked all the way toward the end where the only light was Boston's reflection on the harbor. I moved slowly in their direction, and when I pulled up next to Tom's car, he stepped out to open my car door. I saw the outline of his friend in the back seat of his car. He had a hat tipped down over his head shadowing the majority of his face. I wondered if he was really blindfolded.
"I thought maybe you'd chicken out," said Tom, opening my door for me. His voice was kept low as if he didn't want his friend to hear. In an unusual movement, he put his arms around my waist and pulled me up close to him. I could smell the alcohol on his breath. I welcomed his embrace and the deep kiss that followed. His cock stirred beneath his trousers and I felt heady from deep kiss. When he finally released me, I looked back into his car. I could see the necktie securely fixed as a blindfold.
"Do you think he's ready?" I whispered.
"He's probably already cum in his pants just knowing you're standing out here," he laughed.
I opened the back door and slid in next to Mike. His arm was draped across the back seat and in his hand was the $100 bill. Tom walked around the back of the car and stood on the other side next to door where Mike sat. The window was half down enabling him to see in.
"Hi Mike," I whispered, sliding up close enough to touch his suit jacket. He smelled of cologne and beer. So this was what it was like to be a hooker. I felt empowered by the role change.
"Hi." He smiled nervously and cleared his throat. "Wish I could see you."
"Yes, I know you do, Mike." I let my hand slide softly up his shirt, pressing noticeably on his chest. Then I touched his face and ran my fingers over his lips until he sucked one into his mouth. "But this is how we have to do it tonight." I pulled my hand away and slid it back down his chest and stomach, stopping when I reached his belt.
"I understand you want me to suck your cock," I whispered, moving in a little closer to his ear.
"Oh yeah..." he sighed, shifting his weight nervously in the seat.
"Hmmm," I teased, running my hand over his trousers. "You want that really bad, huh?" His cock was already hard and bent uncomfortably within the confines of his shorts. "Oh yes... feel how hard you are." He moaned and gripped the hand rest on the door to keep from touching me. I was surprised how in control I felt and enjoyed teasing him further.
"I think we should let him stretch out a bit, don't you?" I unbuckled his belt and used both hands to unbutton his pants and open the zipper. His shorts were wet with precum and I rubbed my finger along the fabric.
"Look how excited you are," I purred. I reached in and pulled out his stiff cock, and held it firmly in my hand without stroking it. Mike sucked in a quick breath and held it waiting for more. Tom shifted his position outside the car door and I glanced out the window. From my view point, I could only see his torso. He rubbed his hand over his trousers as he watched.
I moved my hand slowly and stroked Mike's cock as he let out a groan. When I gripped it tighter, he dropped his head back and smiled. "Oh yeah," he moaned. "That feels great."
"But that's not all you want, is it?" I teased, reaching down further and caressing his balls. He shook his head no and scooted down further in the seat to provide more room for my hand. I moved my lips so close to his ear that I knew he could feel my breath. "Tell me what else you want."
Mike turned and tried to kiss me, but I pulled away quickly. I squeezed his cock tight and stroked the shaft.
"Oh God, suck it!" he begged.
"I don't know, Mike. It's awful big." My tone was mischievously innocent and he grinned. "Do you really think I could get that whole thing in my mouth?" I rubbed the precum over the head of his cock and stroked it quickly.
"Please..." he groaned, thrusting his hips toward my hand. "Suck it."
Tom took a step closer to the window as I bent my head toward Mike's cock. I knew he was enjoying the show. I wondered if he could actually see my lips wrapping around Mike's cock as I engulfed it. It was slightly larger than most, providing a challenge to take it all in. But I was determined to earn my money.
Mike's hand finally dropped from the back of the seat, but he obeyed my rules and only touched my hair. But the touching soon turned to grabbing as he manipulated my head over his cock.
"Oh shit!" he hissed, pushing his cock up into my mouth. "Suck it good."
I struggled to maintain a position that allowed me to get enough air on the uptake to withstand the blocked air passage when I took the whole thing down my throat. He was going wild fucking my mouth and my momentary feeling of being in control was vanishing. My only solace was that he was very close to coming.
"Oh Baby," he groaned, grabbing my hair tighter and thrusting his cock deeper into my mouth. "I'm gonna come..." I couldn't respond other than to moan and grip his leg tighter.
"Swallow it, Baby..." he panted quickly, his body about to go out of control.
I squealed in excitement, the vibration shooting through his cock as he came in my mouth. With each jerk he seemed to try to thrust further down my throat and I fought to keep from choking on his sperm. Finally, when the last drop had been savored, he quieted and released his grip on my hair.
"Oh man!" he sighed, his body relaxing into the seat. "You're really good."
I wiped the wetness away from my face as I sat up. Mike had a wistful smile on his face as he caught his breath. Tom was moving back over to my door as I straightened my clothes and hair.
I leaned over and kissed Mike gently on the cheek. "You've been a very good boy, Mike."
He laughed and wiggled the $100 bill in his hand. I plucked it from his fingers and smiled.
"Thank you... and please come again." We both laughed as I turned and stepped out of the car. My panties felt soaked from my own excitement. Tom was visibly anxious as we walked back to my car.
"You okay?" I asked.
"I'm so hard, I can barely walk."
"Oh." I grinned and opened my car door. "Don't worry, Tom. You'll get your finder's fee." I sat down in my car seat, but left my feet outside on the pavement. I tugged on Tom's hand and pulled him up close enough that his crotch was right in front of my face.
"Right here?" he asked in disbelief.
"Yep, right here."
He looked around, feeling vulnerable out in the middle of the parking lot. Mike sat in the car as instructed and waited blindfolded for Tom's return.
"Unless you don't want to," I teased.
He quickly opened his trousers and pulled out his hard cock. It was jerking in excitement. He rushed it toward my mouth quickly and I grabbed it and held him back.
"Easy boy," I laughed. "You could hurt someone with that."
"Oh God, hurry," he begged. "I'm dying here."
I leaned forward and wrapped my lips around the head of his cock. He held onto my shoulders and gently moved his hips forward. When I took it deeper into my mouth, his knees buckled slightly and he gripped my shoulders tighter. Tom was much quieter than Mike and seemed to concentrate harder. His body was the only clue I had as to how close he was to coming.
I reached in with one hand and cupped his balls and played them as he moved his cock in and out of my mouth. At first he wasn't as forceful as Mike had been about me sucking the whole length of his cock, but as he started to shift his weight and tighten his legs he moved closer to my mouth. His hands moved from my shoulders to my hair and before long, he was fucking my mouth as ruthlessly as Mike had. I grabbed his ass and pulled him into me, and held him tightly as he came. Other than a quiet grunt, he was silent as he came. My only clue was the warm cum in my mouth and his jerking body movements.
When he finally quieted, I released his cock with a gentle kiss. I wiped my face as he tucked it gently back into his pants. He pulled me back up to stand next to him and then cradled me in his arms.
"This was wild," he sighed.
"Yes," I laughed. "It was... and I'm so horny I'm about to scream."
"I'd be glad to take care of it."
I looked over at Mike sitting in his car. "Well, you have clients to entertain."
"Trust me," laughed Tom. "He's had all the entertainment he's getting out of me tonight. I'm taking him back to his hotel."
"I've got a better idea." I looked over at Mike and then back to Tom. "Give him the keys to your car and come with me. I'll drop you off at his hotel in the morning on my way into work."
"That's what I love about you," he said turning toward his car. "Your brain!"